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Journal articles on the topic 'Pyrrolo[3,4 c]pyrazole'

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Published: 1 July 2022

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1

Thorimbert, Serge, Candice Botuha, and Kevin Passador. "‘Heteroaromatic Rings of the Future’: Exploration of Unconquered Chemical Space." Synthesis 51, no. 02 (November 7, 2018): 384–98. http://dx.doi.org/10.1055/s-0037-1611279.

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William Pitt and co-workers have created a virtual exploratory heterocyclic library ‘VEHICLe’ containing over 200 unconquered bicyclic heteroaromatic rings, synthetically feasible with potential medicinal interest. Since the publication of the 22 ‘heteroaromatic rings of the future’ by Pitt in 2009, 15 of them have been successfully synthesized as bicyclic or polycyclic forms and evaluated for applications in both biology and material science. This short review presents the critical synthesis associated with innovative synthetic methodologies of the synthetically conquered ring scaffolds from the list of 22 with a spotlight on the scientific contribution of this fascinating article for the expansion of the chemical diversity.1 Introduction2 Heteroaromatic Rings of the Future: The Synthetic challenge?2.1 4-Pyrido[1,3]oxazin-4-one-P1 2.2 Pyrrolo[2,1-b][1,3]oxazin-4-one-P4 2.3 Furo[2,1-e]pyridazin-4(1H)-one-P5 2.4 Isoxazolo[3,4-c]pyridin-7-one-P6 2.5 5H,6H-[1,2]Thiazolo[5,4-c]pyridin-5-one-P7 2.6 4H,5H-Furo[3,2-b]pyridin-5-one-P8 2.7 1H,5H,6H-Pyrazolo[3,4-c]pyridin-5-one-P9 2.8 Thieno[3,4-c]pyridazine-P10 2.9 Pyrrolo[1,2-c][1,2,3]triazine-P11 2.10 Thieno[3,4-a]oxazole-P12 2.11 2,4-Dihydropyrrolo[3,2-c]pyrazole-P13 2.12 Pyrazolo[1,5-b]isoxazole-P14 2.13 Imidazo[1,5-c]pyrimidin-3(2H)-one-P16 2.14 Cyclopenta[b][1,4]oxazin-5(4H)-one-P17 2.15 2,3-Dihydro-2,6-naphthyridin-3-one-P18 3 Conclusion

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2

Patole, Sandip S., and Shankarsing S. Rajput. "MICROWAVE ASSISTED SYNTHESIS AND MICROBIAL EVALUATION OF -2H-PYRROLO [2, 3-C: 5, 4 C'] DIPYRAZOLE-2, 5 (7H)-BIS-CARBOTHIOAMIDE DERIVATIVES." Journal of Advanced Scientific Research 13, no. 01 (February 10, 2022): 135–46. http://dx.doi.org/10.55218/jasr.202213114.

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In this study the synthesis of novel carbothiomides derivatives containing pyrazole moiety have been carried out by use of microwave assisted green and efficient process. The starting compound N-phenyl substituted succinamides 5a-b were condensed with substituted benzaldehydes furnished in to bis-heterocyclic chalcones which on treatment with thiosemicarbazide hydrochloride leads to formation of pyrralo dipyrazole carbothiomide derivatives. The structures of all synthesized compounds were determined by FT IR, 1H NMR, 13CNMR spectral analysis techniques. The pyrazole carbothiomide derivatives were selected for evaluation of antimicrobial activities. The in vitro antibacterial screening was carried out against Gram positive bacteria Staphylococcus auras, Bacillus subtilis and Gram negative bacteria Pseudomonas aeruginosa, Escherichia coli. The antibacterial activity was measured in term of zone of inhibition in mm unit and compared with standard antibiotic drug Chloramphenicol. Similarly antifungal evaluation was also evaluated in vitro against fungi Aspergillus niger and Candida albicans. The zone of inhibition was measured in mm and compared with standard antifungal drug Amphotericin-B. The all carbothiomide derivatives showed good anti-bacterial activities against gram positive bacteria and good anti-fungal activities. The compounds 9ai and 9aiv showed potent antifungal activity against Candida albicans than standard drug amphotericin-B at 100 μgm/mL concentration.

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3

Perrin, Monique, Alain Thozet, Pilar Cabildo, Rosa Ma Claramunt, Eduard Valenti, and José Elguero. "Molecular structure and tautomerism of 3,5-bis(4-methylpyrazol-1-yl)-4-methylpyrazole." Canadian Journal of Chemistry 71, no. 9 (September 1, 1993): 1443–49. http://dx.doi.org/10.1139/v93-186.

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The title compound C12N6H14, 1, crystallizes in the space group P21/n (a = 8.222(2) Å, b = 27.336(8) Å, c = 5.574(2) Å, α = 90.00°, β = 100.97(4)°, γ = 90.00°), Z = 4, d = 1.308 g cm−3. The conformation about the N—C bonds linking the pyrazole rings can be defined as EZ, with "pyridine-like" nitrogen atoms in an anti disposition [Formula: see text] and "pyridine-like" and "pyrrole-like" nitrogen atoms in a syn disposition [Formula: see text] with regard to the central pyrazole. Intermolecular hydrogen bonds between the central and the terminal pyrazole ring of configuration Z form centrosymmetric dimers. They pack in sheets nearly parallel to the (−2 3 1) plane. Its tautomerization barrier has been determined in methanol-d4; the value, 11.9 kcal mol−1, is similar to those of 3,5-dimethyl-4-chloropyrazole (12.8 kcal mol−1) and 3,5-dimethyl-4-nitropyrazole (12.1 kcalmol−1). These values together with the shape of the conformational potential surface (calculated using the AM1 Hamiltonian) suggest that, in compound 1, prototropy and rotation about the N—C bonds linking the three pyrazole rings take place simultaneously.

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4

Das, Joydip. "Novel N-pyrimidin-4-yl-3-amino-pyrrolo [3, 4-C] pyrazole derivatives as PKC kinase inhibitors: a patent evaluation of US2015099743 (A1)." Expert Opinion on Therapeutic Patents 26, no. 4 (December 14, 2015): 523–28. http://dx.doi.org/10.1517/13543776.2015.1124088.

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5

Avasthi, Kamlakar, Lakshmi Shukla, Ruchir Kant, and Krishnan Ravikumar. "Folded conformations due to arene interactions in dissymmetric and symmetric butylidene-linker models based on pyrazolo[3,4-d]pyrimidine, purine and 7-deazapurine." Acta Crystallographica Section C Structural Chemistry 70, no. 6 (May 9, 2014): 555–61. http://dx.doi.org/10.1107/s2053229614009449.

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The butylidene-linker models 1-[2-(2,6-dimethylsulfanyl-9H-purin-9-yl)-2-methylidenepropyl]-4,6-bis(methylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidine, C18H20N8S4, (XI), 7,7′-(2-methylidenepropane-1,3-diyl)bis[3-methyl-2-methylsulfanyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one], C20H22N6O2S2, (XIV), and 7-[2-(4,6-dimethylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-2-methylidenepropyl]-3-methyl-2-methylsulfanyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one, C19H21N7OS3, (XV), show folded conformations in solution, as shown by1H NMR analysis. This folding carries over to the crystalline state. Intramolecular π–π interactions are observed in all three compounds, but only (XIV) shows additional intramolecular C—H...π interactions in the solid state. As far as can be established, this is the first report incorporating the pyrrolo[2,3-d]pyrimidine nucleus for such a study. In addition to the π–π interactions, the crystal structures are also stabilized by other weak intermolecular C—H...S/N/O and/or S...N/S interactions.

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6

Mague, Joel T., Shaaban K. Mohamed, Mehmet Akkurt, Talaat I. El-Emary, and Mustafa R. Albayati. "Crystal structure of 3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazole-4-carbaldehyde." Acta Crystallographica Section E Structure Reports Online 70, no. 10 (September 27, 2014): o1131—o1132. http://dx.doi.org/10.1107/s1600536814020984.

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In the title compound, C15H13N3O, the pyrrolyl and phenyl rings make dihedral angles of 58.99 (5) and 34.95 (5)°, respectively, with the central pyrazole ring. In the crystal, weak, pairwise C—H...O interactions across centers of symmetry form dimers, which are further associated into corrugated sheets running approximately parallel to (100)viaweak C—H...N interactions.

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Mague, Joel T., Shaaban K. Mohamed, Mehmet Akkurt, Hussein M. S. El-Kashef, and Mustafa R. Albayati. "Crystal structure of (E)-4-{[2-(2,4-dinitrophenyl)hydrazin-1-ylidene]methyl}-3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazole." Acta Crystallographica Section E Structure Reports Online 70, no. 12 (November 8, 2014): o1246—o1247. http://dx.doi.org/10.1107/s1600536814024039.

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The title compound, C21H17N7O4, is in an `extended' conformation aided by an intramolecular N—H...O hydrogen bond. The pyrazole ring makes dihedral angles of 29.17 (6), 65.47 (4) and 9.91 (7)°, respectively, with the phenyl, pyrrole and benzene rings. In the crystal, molecules are connected by pairs of N—H...O and C—H...O hydrogen bonds, forming inversion dimers which associate into ribbons running along thebaxis through complementary C—H...O interactions.

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8

Gašparová, Renáta, Martin Moncman, and Branislav Horváth. "Microwave assisted reactions of 2-[3-(Trifluoromethyl)phenyl]-4-R1-furo[3,2-b] pyrrole-5-carboxhydrazides." Open Chemistry 6, no. 2 (June 1, 2008): 180–87. http://dx.doi.org/10.2478/s11532-008-0009-4.

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AbstractThe effect of microwave irradiation on the reactions of 2-[3-(trifluoromethyl)phenyl]-4-R1-furo[3,2-b]pyrrole-5-carboxhydrazides 1 with 5-arylfuran-2-carboxaldehydes 2, thiophene-2-carboxaldehyde (3) and methyl 2-formylfuro[3,2-b]pyrrole-5-carboxylates 4 has been studied. Reactions of 1 with formic and acetic acid, respectively, led to acylhydrazides 9a–c. Reaction of 1a with 4-substituted 1,3-oxazol-5(4H)-one 10 led to imidazole derivative 13. 1,2,4-Triazole-3-thiones 15a,b were synthesized by two-step reaction of 1a with potassium isothiocyanate and phenyl isothiocyanate, respectively, and subsequent base-catalyzed cyclization of thiosemicarbazides 14a,b. Pyrazole 16 was prepared by reaction of 1a with pentane-2,4-dione.

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KAUR, MANPREET, BALDEV SINGH, and BALJIT SINGH. "1, 3-Dipolar cycloaddition reactions: Synthesis of 5-benzyl-1-(2′,4′-dibromophenyl)-3-(4″-substituted phenyl)-3a,4,6,6a-tetrahydro-1H, 5H-pyrrolo[3,4-c]pyrazole-4,6-dione derivatives." Journal of Chemical Sciences 125, no. 6 (November 2013): 1529–34. http://dx.doi.org/10.1007/s12039-013-0526-3.

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Mague, Joel T., Shaaban K. Mohamed, Mehmet Akkurt, Talaat I. El-Emary, and Mustafa R. Albayati. "Crystal structure of (E)-N-{[3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazol-4-yl]methylidene}hydroxylamine." Acta Crystallographica Section E Structure Reports Online 70, no. 11 (October 31, 2014): o1216—o1217. http://dx.doi.org/10.1107/s1600536814023514.

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The title compound, C15H14N4O, crystallizes with two molecules in the asymmetric unit with similar conformations (r.m.s. overlay fit for the 20 non-H atoms = 0.175 Å). In the first molecule, the dihedral angles between the planes of the central pyrazole ring and the pendant phenyl and pyrrole rings are 42.69 (8) and 51.88 (6)°, respectively, with corresponding angles of 54.49 (7) and 49.61 (9)°, respectively, in the second molecule. In the crystal, the two molecules, together with their inversion-symmetry counterparts, are linked into tetramers by O—H...N hydrogen bonds. The tetramers form layers parallel to (211) through pairwise C—H...π interactions.

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11

Zhang, Yan, and Xin-Xiang Lei. "Crystal structure of hexahydro-7-hydroxy-3-(2-methylpropyl)pyrrolo [1,2-a]pyrazine-1,4-dione, C11H18N2O3." Zeitschrift für Kristallographie - New Crystal Structures 230, no. 3 (September 1, 2015): 199–200. http://dx.doi.org/10.1515/ncrs-2014-9061.

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12

Kaur, Manpreet, Baldev Singh, and Baljit Singh. "ChemInform Abstract: 1,3-Dipolar Cycloaddition Reactions: Synthesis of 5-Benzyl-1-(2′,4′-dibromophenyl)-3-(4′′-substituted phenyl)-3a,4,6,6a-tetrahydro-1H,5H-pyrrolo[3,4-c]pyrazole-4,6-dione Derivatives." ChemInform 45, no. 18 (April 17, 2014): no. http://dx.doi.org/10.1002/chin.201418117.

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13

Ganapathy, Jagadeesan, M. Pramesh, P. T. Perumal, and Aravindhan Sanmargam. "Structural Analysis of 2-Benzyl-3-[3-(4-bromo-phenyl)-1-phenyl-1H-pyrazol-4yl]-4,6-dioxo-5-phenyl-octahydro-pyrrolo[3,4-C]pyrrole-1-carboxylic Acid Ethyl Ester through X-ray Crystallography." Journal of the Chosun Natural Science 8, no. 3 (September 30, 2015): 192–203. http://dx.doi.org/10.13160/ricns.2015.8.3.192.

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14

Mohamed, Shaaban K., Awad I. Said, Joel T. Mague, Talaat I. El-Emary, Mehmet Akkurt, and Sahar M. I. Elgarhy. "Crystal structure and Hirshfeld surface analysis of (3S,3aR,6aS)-3-(1,3-diphenyl-1H-pyrazol-4-yl)-5-(4-methoxyphenyl)-2-phenyl-3,3a,4,5,6,6a-hexahydro-2H-pyrrolo[3,4-d][1,2]oxazole-4,6-dione." Acta Crystallographica Section E Crystallographic Communications 77, no. 4 (March 5, 2021): 356–59. http://dx.doi.org/10.1107/s2056989021002358.

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In the title compound, C33H26N4O4, the two fused five-membered rings and their N-bound aromatic substituents form a pincer-like motif. The relative conformations about the three chiral carbon atoms are established. In the crystal, a combination of C—H...O and C—H...N hydrogen bonds and C—H...π(ring) interactions leads to the formation of layers parallel to the bc plane. A Hirshfeld surface analysis indicates that the most significant contributions to the crystal packing are from H...H (44.3%), C...H/H...C (29.8%) and O...H/H...O (15.0%) contacts.

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15

Foize Ahmad, G., A. Syed Mohammed Mujaheer, M. NizamMohideen, M. Gulam Mohamed, and V. Viswanathan. "The crystal structures and Hirshfeld surface analysis of 6-(naphthalen-1-yl)-6a-nitro-6,6a,6b,7,9,11a-hexahydrospiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,11′-indeno[1,2-b]quinoxaline] and 6′-(naphthalen-1-yl)-6a′-nitro-6′,6a′,6b′,7′,8′,9′,10′,12a′-octahydro-2H-spiro[acenaphthylene-1,12′-chromeno[3,4-a]indolizin]-2-one." Acta Crystallographica Section E Crystallographic Communications 75, no. 10 (September 27, 2019): 1519–24. http://dx.doi.org/10.1107/s205698901901291x.

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The title compounds, 6-(naphthalen-1-yl)-6a-nitro-6,6a,6 b,7,9,11a-hexahydrospiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,11′-indeno[1,2-b]quinoxaline], C37H26N4O3S, (I), and 6′-(naphthalen-1-yl)-6a′-nitro-6′,6a′,6b′,7′,8′,9′,10′,12a′-octahydro-2H-spiro[acenaphthylene-1,12′-chromeno[3,4-a]indolizin]-2-one, C36H28N2O4, (II), are new spiro derivatives, in which both the pyrrolidine rings adopt twisted conformations. In (I), the five-membered thiazole ring adopts an envelope conformation, while the eight-membered pyrrolidine-thiazole ring adopts a boat conformation. An intramolecular C—H...N hydrogen bond occurs, involving a C atom of the pyran ring and an N atom of the pyrazine ring. In (II), the six-membered piperidine ring adopts a chair conformation. An intramolecular C—H...O hydrogen bond occurs, involving a C atom of the pyrrolidine ring and the keto O atom. For both compounds, the crystal structure is stabilized by intermolecular C—H...O hydrogen bonds. In (I), the C—H...O hydrogen bonds link adjacent molecules, forming R 2 2(16) loops propagating along the b-axis direction, while in (II) they form zigzag chains along the b-axis direction. In both compounds, C—H...π interactions help to consolidate the structure, but no significant π–π interactions with centroid–centroid distances of less than 4 Å are observed.

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Khan, Ayad Kareem. "Synthesis, Identification and Anti-candidaProperties of Some NewBis (Five, Six, Seven-membered Heterocycles) AttachedPyrrole Rings." Al Mustansiriyah Journal of Pharmaceutical Sciences 17, no. 1 (March 13, 2018): 16. http://dx.doi.org/10.32947/ajps.v17i1.74.

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This research involves preparation of many bisheterocycles attached to pyrrole rings have been synthesized by the stepwise procedure such asbis(1,2-dihydropyridazine-3,6-dione) (3),bis(2,3dihydrophthalazine-1,4-dione) (4) and bis(tetrahydropyridazine-3,6-dione) (5) derivatives of pyrrole. Further the bis(3,5-dimethyl-1H-pyrazol-1-yl)methanone (6), bis(3-methyl-1H-pyrazol5(4H)-one) (7) and bis(4H-1,3,4-oxadiazin-6(5H)-one) (8) pyrrole derivatives also prepared in good yields. Furthermore, series of bis-benzothiazine (10a-c), bis-benzoxathiazepine (11a-c)and bis-quinazoline compounds (12a-c) attached to pyrrole moieties also have been synthesized successfully.Structures of the newly synthesized compounds were established by physicochemical, elemental analysis CHNS, FTIR, H-NMR and C-NMR spectroscopic methods. The new synthesized agents were evaluated for their in vitro inhibitory effectagainst several candida isolates. Some of the evaluated compounds possessed good activities compared to a fluconazole, nystatin and clotrimazole standard antifungal drugs.

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17

Murugan, J., J. Haribabu, B. S. R. Reddy, G. Rajarajan, and S. Murugavel. "(6′R*,7′R*)-7′-(1,3,-Diphenyl-1H-pyrazol-4-yl)-1,2,5′,6′,7′,7a',3′′,4′′-octahydro-1′H,2′′H-dispiro[acenaphthylene-1,5′-pyrrolo[1,2-c][1,3]thiazole-6′,3′′-[1]benzopyran]-2,4′′-dione." Acta Crystallographica Section E Structure Reports Online 69, no. 4 (March 6, 2013): o493—o494. http://dx.doi.org/10.1107/s1600536813005825.

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18

Quiroga, Jairo, Jaime Gálvez, Justo Cobo, and Christopher Glidewell. "Two methyl 3-(1H-pyrazol-4-yl)octahydropyrrolo[3,4-c]pyrrole-1-carboxylates form different hydrogen-bonded sheets." Acta Crystallographica Section C Crystal Structure Communications 69, no. 8 (July 13, 2013): 915–19. http://dx.doi.org/10.1107/s0108270113017563.

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In the molecules of both methyl (1RS,3SR,3aRS,6aSR)-1-methyl-3-(3-methyl-1-phenyl-1H-pyrazol-4-yl)-4,6-dioxo-5-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate, C25H24N4O4, (I), and methyl (1RS,3SR,3aRS,6aSR)-5-(4-chlorophenyl)-1-methyl-3-(3-methyl-1-phenyl-1H-pyrazol-4-yl)-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1-carboxylate, C25H23ClN4O4, (II), the two rings of the pyrrolopyrrole fragment are both nonplanar, with conformations close to half-chair forms. The overall conformations of the molecules of (I) and (II) are very similar, apart from the orientation of the ester function. The molecules of (I) are linked into sheets by a combination of an N—H...π(pyrrole) hydrogen bond and three independent C—H...O hydrogen bonds. The molecules of (II) are also linked into sheets, which are generated by a combination of an N—H...N hydrogen bond and two independent C—H...O hydrogen bonds, weakly augmented by a C—H...π(arene) hydrogen bond.

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Hafez Taghva, Pardis, and Hassan Kabirifard. "Ring-chain transformation of 4-aroyl-5-phenylamino-2,3-dihydrothiophene-2,3-diones: Facile and efficient synthesis of novel pyrrolo[2,3-c]pyrazol-3(2H)-ones and 1,2-dihydro-5H,6H-pyridazine-5,6-diones." Journal of Sulfur Chemistry 41, no. 2 (December 15, 2019): 200–209. http://dx.doi.org/10.1080/17415993.2019.1702664.

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Kannan, Piskala Subburaman, Devaraj Kathirvelan, Boreddy Siva Rami Reddy, Elumalai Govindan, and Arunachalathevar SubbiahPandi. "6′-(1,3-Diphenyl-1H-pyrazol-4-yl)-7′-(1H-indol-3-ylcarbonyl)-2-oxo-1-(prop-2-en-1-yl)-5′,6′,7′,7a'-tetrahydro-1′H-spiro[indoline-3,5′-pyrrolo[1,2-c][1,3]thiazole]-7′-carbonitrile." Acta Crystallographica Section E Structure Reports Online 69, no. 6 (May 11, 2013): o857—o858. http://dx.doi.org/10.1107/s1600536813011513.

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21

Bai, Xiao-Guang, Ju-Xian Wang, and Yu-Cheng Wang. "N-(1-Acetyl-5-benzoyl-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3-yl)benzamide." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (May 12, 2012): o1677. http://dx.doi.org/10.1107/s1600536812019708.

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In the molecule of the title compound, C21H18N4O3, the fused pyrrolo[3,4-c]pyrazole ring system is approximately planar [maximum deviation = 0.0486 (16) Å] and forms dihedral angles of 87.21 (8) and 35.46 (7)° with the phenyl rings. In the crystal, N—H...O and C—H...O hydrogen bonds and weak C—H...π interactions link the molecules into chains parallel to [201].

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22

Anizon, Fabrice, Bruno Pfeiffer, and Michelle Prudhomme. "Synthesis of pyridino[3′,2′:4,5]pyrrolo[3,2-g]pyrrolo[3,4-e]indolizin-1,3-dione and pyrrolo[3,2-c]pyrazole skeletons." Tetrahedron Letters 47, no. 4 (January 2006): 433–36. http://dx.doi.org/10.1016/j.tetlet.2005.11.076.

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23

Gein, Vladimir L., and Evgenia V. Pastukhova. "Synthesis and properties of 1-aminocarbonylmethyl-5-aryl- 4-aroyl-3-hydroxy-3-pyrroline-2-ones." Butlerov Communications 64, no. 10 (October 31, 2020): 28–32. http://dx.doi.org/10.37952/roi-jbc-01/20-64-10-28.

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3-Hydroxy-3-pyrrolin-2-ones are fully hydrogenated heterocyclic compounds, the base of which is included in a number of biologically active substances and drugs. Scientists' interest in 3-Hydroxy-3-pyrrolin-2-ones is due to the fact that, with their availability and high stability, they also have high reactivity due to the active carbonyl group in the third position of the heterocycle and easily interact with moconucleophiles. In addition, the presence of acyl and ethoxycarbonyl groups in the fourth position of the heterocycle makes it possible to obtain various condensed systems in reactions with binucleophiles, thereby making it possible to expand the range of the indicated compounds. We set the task to prepare 5-aryl-4-acyl-3-hydroxy-3-pyrrolin-2-ones containing an amino-carbonylmethyl substituent in the first position of the heterocycle, which were not previously described in the literature. It was also supposed to establish how the obtained compounds react with hydrazine hydrate. A series of 1-aminocarbonylmethyl-5-aryl-4-aroyl-3-hydroxy-3-pyrrolin-2-ones was obtained by setting up a three-component reaction of aroylpyruvic acid methyl ester with aromatic aldehydes and glycinamide hydrochloride in glacial acetic acid. The structure of the obtained compounds was established on the basis of IR and 1H NMR spectroscopy data. Based on the data of 1H NMR spectroscopy and a positive reaction with an alcoholic solution of iron(III) chloride, the predominant existence of the obtained compounds in the enol form was established. The article describes the mechanism of three-component reactions, the structural formulas of the obtained compounds, their physicochemical properties and spectral characteristics, as well as the yields of the reaction products. We have also studied the interaction of 1-substituted 5-aryl-4-acyl-3-hydroxy-3-pyrrolin- 2-ones with such a binucleophilic reagent as hydrazine hydrate. As a result of refluxing 1-amino-carbonylmethyl-3-hydroxy-4-(4-methoxybenzoyl)-5-(2-chlorophenyl)-3-pyrrolin-2-one and hydrazine hydrate in glacial acetic acid, 2-[4-(2-chlorophenyl)-3-(4-methoxyphenyl)-6-oxo-4,6-dihydropyrrolo [3,4-c] pyrazol-5(1H)-yl] acetamide. The article describes the proposed reaction mechanism, product yield, its physicochemical properties and spectral characteristics.

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Kamatchi, P., G. Jagadeesan, M. Pramesh, P. T. Perumal, and S. Aravindhan. "Ethyl 2-benzyl-3-[3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl]-4,6-dioxo-5-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate." Acta Crystallographica Section E Structure Reports Online 68, no. 2 (January 31, 2012): o552. http://dx.doi.org/10.1107/s1600536812002450.

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25

Yousuf, Sammer, Huma Bano, Munira Taj Muhammad, and Khalid Mohammed Khan. "Crystal structure of 6-amino-4-(3-bromo-4-methoxyphenyl)-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile dimethyl sulfoxide monosolvate." Acta Crystallographica Section E Crystallographic Communications 71, no. 7 (June 6, 2015): o453—o454. http://dx.doi.org/10.1107/s2056989015010543.

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In the pyrazole molecule of the title solvate, C15H13BrN4O2·C2H6OS, the dihedral angle between the benzene ring and the mean plane of the dihydropyrano[2,3-c]pyrazole ring system [r.m.s deviation = 0.031 (2) Å] is 86.71 (14)°. In the crystal, the pyrazole molecules are linked by N—H...N hydrogen bonds, forming a layer parallel to (10-1). The pyrazole and dimethyl sulfoxide molecules are connected by an N—H...O hydrogen bond.

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26

Abdel-Aziz, Hatem A., Hazem A. Ghabbour, Suchada Chantrapromma, and Hoong-Kun Fun. "3-Acetyl-1,5-diphenyl-1H-pyrazole-4-carbonitrile." Acta Crystallographica Section E Structure Reports Online 68, no. 4 (March 17, 2012): o1095—o1096. http://dx.doi.org/10.1107/s1600536812010938.

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The title compound, C18H13N3O, has a butterfly-like structure, in which the pyrazole ring forms dihedral angles of 59.31 (8) and 57.24 (8)° with the two phenyl rings. The dihedral angle between the two phenyl rings is 64.03 (8)°. The pyrazole ring and the C—C=O plane of the acetyl group are twisted slightly, making a dihedral angle of 7.95 (18)°. In the crystal, molecules are linked through weak C—H...N and C—H...O interactions into a helical chain along thea-axis direction.

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27

Dawood, Kamal M., Eman A. Ragab, and Sanaa N. Mohamed. "Synthesis of Some New Indolizine and Pyrrolo[1,2-a]quinoline Derivatives via Nitrogen Ylides." Zeitschrift für Naturforschung B 64, no. 4 (April 1, 2009): 434–38. http://dx.doi.org/10.1515/znb-2009-0413.

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Pyridine and quinoline react with 3-bromoacetyl-1,5-diphenyl-1H-pyrazole-4-carbonitrile (2) in dry benzene to give the corresponding pyridinium and quinolinium salts 3 and 9. The latter salts undergo [3+2] 1,3-dipolar cycloaddition with some acetylene and ethylene derivatives to give the corresponding indolizine and pyrrolo[1,2-a]quinoline derivatives

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28

Tewari, Ashish Kumar, Priyanka Srivastava, Ved P. Singh, Praveen Singh, Ranjeet Kumar, Ranjana S. Khanna, Pankaj Srivastava, Ramachandran Gnanasekaran, and Pavel Hobza. "Selective induced polarization through electron transfer in acetone and pyrazole ester derivatives via C–H⋯OC interaction." New J. Chem. 38, no. 10 (2014): 4885–92. http://dx.doi.org/10.1039/c4nj00679h.

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A set of organic compounds (pyrazole ester derivatives,viz.5-[3-(substituted)-propoxy]-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid methyl ester and 5-[2-(substituted)-ethoxy]-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid methyl ester) was synthesized and their affinity and stability towards the acetone molecule were tested by NMR.

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29

Kanjana-opas, Akkharawit, Somrak Panphon, Hoong-Kun Fun, and Suchada Chantrapromma. "4-Methyl-3H-pyrrolo[2,3-c]quinoline." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (June 14, 2006): o2728—o2730. http://dx.doi.org/10.1107/s1600536806021088.

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The title compound, C12H10N2, is a new marine natural product which was isolated for the first time from a novel marine gliding bacterium. The asymmetric unit contains a pair of achiral molecules. Both the molecules are essentially planar and they form a dihedral angle of 83.81 (3)°. In the crystal structure, the molecules exist as N—H...N hydrogen-bonded tetramers.

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30

Adam, Farook, Seranthimata Samshuddin, Nadiah Ameram, Subramaya, and Laxminarayana Samartha. "Crystal structure of 5-[4-(dimethylamino)phenyl]-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde." Acta Crystallographica Section E Crystallographic Communications 71, no. 12 (December 1, 2015): o1031—o1032. http://dx.doi.org/10.1107/s2056989015023294.

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The title compound, C19H21N3O, comprises a central pyrazole ring which is N-connected to an aldehyde group and C-connected twice to substituted benzene rings. The pyrazole ring is twisted on the C—C single bond, and the least-squares plane through this ring forms dihedral angles of 82.44 (5) and 4.52 (5)° with the (dimethylamino)benzene andp-tolyl rings, respectively. In the crystal, weak C—H...O hydrogen bonds link molecules into supramolecular tubes along thebaxis.

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31

Farrukh, Muhammad A., Shaaban K. Mohamed, Maqsood Ahmed, Adel A. Marzouk, and Samir M. El-Moghazy. "4-[5-(4-Chlorophenyl)-3-methyl-1H-pyrazol-1-yl]benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 69, no. 2 (January 26, 2013): o295—o296. http://dx.doi.org/10.1107/s1600536813002134.

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In the title compound, C16H14ClN3O2S, the dihedral angle between the benzene and pyrazole rings is 52.75 (2)°, while that between the pyrazole and 4-chlorophenyl rings is 54.0 (3)°. The terminal sulfonamide group adopts an approximately tetrahedral geometry about the S atom with a C—S—N angle of 108.33 (10)°. In the crystal, pairs of N—H...N hydrogen bonds lead to the formation of inversion dimers. These dimers are linkedviaa second pair of N—H...N hydrogen bonds and C—H...O interactions, forming a two-dimensional network lying parallel to thebcplane. The two-dimensional networks are linkedviaC—H...Cl interactions, forming a three-dimensional structure.

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32

Abdel-Wahab, Bakr F., Ehab Abdel-Latif, Seik Weng Ng, and Edward R. T. Tiekink. "5-(4-Fluorophenyl)-3-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]-4,5-dihydro-1H-pyrazole-1-carbothioamide." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (May 31, 2012): o1954—o1955. http://dx.doi.org/10.1107/s1600536812024245.

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In the title compound, C20H19FN6S, the pyrazole ring has an envelope conformation, with the methine C atom being the flap atom. The dihedral angle between the least-squares plane through the pyrazole and triazole rings is 7.59 (9)°, and the triazole and attached benzene ring form a dihedral angle of 74.79 (9)°. The thiourea group is coplanar with the pyrazole ring [N—N—C—S torsion angle = −179.93 (11)°], which enables the formation of an intramolecular N—H...N hydrogen bond. In the crystal, inversion-related molecules associate via N—H...S hydrogen bonds and eight-membered {...HNCS}2 synthons feature in the crystal packing. These synthons are connected into supramolecular chains along the a axis via N—H...F hydrogen bonds, and the chains are consolidated into layers in the ab plane via C—H...S and C—H...F contacts.

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33

Kaur, Manpreet, Jerry P. Jasinski, H. S. Yathirajan, B. Narayana, and K. Byrappa. "N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-(4-nitrophenyl)acetamide." Acta Crystallographica Section E Structure Reports Online 70, no. 6 (May 3, 2014): o636—o637. http://dx.doi.org/10.1107/s1600536814009738.

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In the title compound, C19H18N4O4, the nitrophenyl and phenyl rings are twisted by 67.0 (6) and 37.4 (4)°, respectively, with respect to the pyrazole ring plane [maximum deviation = 0.0042 (16) Å]. The dihedral angle between the mean planes of the phenyl rings is 59.3 (3)°. The amide group, with a C—N—C—C torsion angle of 177.54 (13)°, is twisted away from the plane of the pyrazole ring in an antiperiplanar conformation. In the crystal, N—H...O hydrogen bonds involving the carbonyl group on the pyrazole ring and the amide group, together with weak C—H...O interactions formingR22(10) graph-set motifs, link the molecules into chains along [100]. Additional weak C—H...O interactions involving the nitrophenyl rings further link the molecules along [001], also formingR22(10) graph-set motifs, thereby generating (010) layers.

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34

Abdelrazek, Fathy Mohamed, Ayman Wahba Erian, and Khalid Mohamed Hassan Hilmy. "Nitriles in Heterocyclic Synthesis. A Novel Synthesis of 4-Phenacylpyrazole and Pyrrolo[2,3-c]pyrazole Derivatives." Synthesis 1986, no. 01 (1986): 74–75. http://dx.doi.org/10.1055/s-1986-31484.

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35

Chopra, Deepak, T. P. Mohan, and B. Vishalakshi. "1-Acetyl-3-(4-chlorophenyl)-5-(4-fluoro-3-phenoxyphenyl)-1H-pyrazole." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (June 14, 2006): o2770—o2772. http://dx.doi.org/10.1107/s1600536806020046.

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In the title compound, C23H18ClFN2O2, the dihedral angles between the pyrazole ring and the attached chlorophenyl ring, the planar acetyl group and the fluorobenzene ring of the phenoxyphenyl unit are 3.3 (1), 5.2 (2) and 74.9 (1)°, respectively. The crystal structure is stabilized by intermolecular C—H...O hydrogen bonds and a short Cl...F contact.

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36

Adam, Farook, Seranthimata Samshuddin, Shruthi, Badiadka Narayana, and Nadiah Ameram. "Crystal structure of 5-(4-methoxyphenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde." Acta Crystallographica Section E Crystallographic Communications 71, no. 12 (December 1, 2015): o1093—o1094. http://dx.doi.org/10.1107/s2056989015023658.

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In the title compound, C18H18N2O2, the pyrazole ring has a twisted conformation on the CH—CH2bond. The tolyl ring and the 4-methoxyphenyl ring are inclined to the mean plane of the pyrazole ring by 4.40 (9) and 86.22 (9)°, respectively, while the two aromatic rings are inclined to one another by 88.75 (9)°. In the crystal, molecules are linkedviabifurcated C—H...(O,O) hydrogen bonds and C—H...π interactions, forming sheets lying parallel to theabplane.

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37

Deeb, Ali, Besher Bayoumy, Fathy Yasine, and Rida Fikry. "Pyridazine Derivatives and Related Compounds, Part 4. Pyrrolo[2,3-c]pyridazines and Furo[2,3-c]pyndazines, Synthesis and Some Reactions." Zeitschrift für Naturforschung B 47, no. 3 (March 1, 1992): 418–23. http://dx.doi.org/10.1515/znb-1992-0320.

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Ethyl 5-amino-3,4-diphenyl-7H-pyrrolo[2,3-c]pyridazine-6-carboxylate (1), ethyl 5-aminofuro[ 2,3-c]pyridazine-6-carboxylate (2) and 5-aminofuro[2,3-c]pyridazine-6-carboxamide (3), are obtained from 4-cyano-5,6-diphenyl-3(2H)-pyridazinone. 5-Acetamido and 5-chloroacetamido derivatives prepared from 1, undergo cyclization on heating to form 2-substituted pyridazino[4',3':4,5]pyrrolo[3,2-d]oxazin-4(5H)-one (5a, b). The reaction of 1 and 2 with hydrazine gave 6-carbohydrazide derivatives (7 a, b). Compound 3 undergoes condensation with acetyl chloride, chloroacetyl chloride, benzoyl chloride, formamide and carbon disulphide to furnish the corresponding pyrimido[4',5' :4,5]furo[2,3-c]pyridazin-4(3 H)-one derivatives. The reaction of 1 with o-aminophenol gave 3,4-diphenyl-11-oxo-10,11-dihydro-12H -pyridazino[ 4',3' :4,5]pyrrolo[3,2-b][1,5]benzoxazepine.

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38

Shaabani, Ahmad, Mohammad Taghi Nazeri, Hassan Farhid, Siamak Javanbakht, and Behrouz Notash. "Highly Efficient Chemoselective Synthesis of Pyrrolo[2,3-c]pyrazole Bearing Oxindole via Sequential Condensation–Michael Addition–Intramolecular Cyclization Reactions." Synlett 31, no. 10 (April 7, 2020): 965–71. http://dx.doi.org/10.1055/s-0039-1690887.

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An efficient and highly chemoselective approach for the synthesis of novel scaffolds based on pyrrolo[2,3-c]pyrazole bearing oxindole is accomplished by the acid-promoted sequential reactions between benzoylacetonitriles, phenylhydrazine, and 3-phenacylideneoxindoles as readily available starting materials. This value structure is dexterously embraced with oxindole, pyrrole, and pyrazole heterocycles, which are famous for their enriched biological properties. Besides, this is an eco-friendly and atom-economy approach, and water is the only side product of the reaction. In this protocol, the requirement of column chromatography is completely avoided, and the products were isolated by recrystallization in crude reactions. These compounds due to their excellent fluorescence features and bioactive scaffolds may be attracted great interest in biomedical applications and clinical diagnostics in the future.

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39

Vinutha, N., S. Madan Kumar, S. Shobhitha, B. Kalluraya, N. K. Lokanath, and D. Revannasiddaiah. "5-(4-Chlorophenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde." Acta Crystallographica Section E Structure Reports Online 70, no. 5 (April 16, 2014): o560. http://dx.doi.org/10.1107/s1600536814007879.

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In the title compound, C17H13ClN2O2, the phenyl and chlorobenzene rings are inclined to the central pyrazole ring at 40.84 (9) and 65.30 (9)°, respectively. In the crystal, pairs of C—H...π interactions link the molecules into inversion dimers and C—H...O hydrogen bonds link these dimers into columns extended in [010]. The crystal packing exhibits short intermolecular O...Cl contacts of 3.0913 (16) Å.

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40

Poornachandran, Mahalingam, and Raghavachary Raghunathan. "Synthesis of pyrrolo[3,4-b]pyrroles and perhydrothiazolo[3′,4′-2,3]pyrrolo[4,5-c]pyrroles." Tetrahedron 64, no. 27 (June 2008): 6461–74. http://dx.doi.org/10.1016/j.tet.2008.04.063.

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41

Fun, Hoong-Kun, Suhana Arshad, Shridhar Malladi, Arun M. Isloor, and Kammasandra Nanjunda Shivananda. "4-[3-(Biphenyl-4-yl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-yl]-3-(4-methoxyphenyl)-1-phenyl-1H-pyrazole dioxane monosolvate." Acta Crystallographica Section E Structure Reports Online 68, no. 4 (March 7, 2012): o972—o973. http://dx.doi.org/10.1107/s1600536812009117.

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In the title compound, C37H30N4O·C4H8O2, the dihedral angle between the pyrazole and dihydropyrazole rings is 74.09 (10)°. In the crystal, the components are linked into centrosymmetric tetramers (two main molecules and two solvent molecules) by C—H...O hydrogen bonds. C—H...π and π–π [shortest centroid-centroid separation = 3.6546 (9) Å] interactions are also observed.

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42

Lipson, Victoria V., Tetiana L. Pavlovska, Nataliya V. Svetlichnaya, Anna A. Poryvai, Nikolay Yu Gorobets, Erik V. Van der Eycken, Irina S. Konovalova, et al. "Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds." Beilstein Journal of Organic Chemistry 15 (May 6, 2019): 1032–45. http://dx.doi.org/10.3762/bjoc.15.101.

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The unexpectedly uncatalyzed reaction between 2-amino-4-arylimidazoles, aromatic aldehydes and Meldrum’s acid has selectively led to the corresponding Knoevenagel–Michael adducts containing a free amino group in the imidazole fragment. The adducts derived from Meldrum’s acid have been smoothly converted into 1,7-diaryl-3-amino-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-ones and 3-(2-amino-4-aryl-1H-imidazol-5-yl)-3-arylpropanoic acids. The interaction of 2-amino-4-arylimidazoles with aromatic aldehydes or isatins and acyclic methylene active compounds has led to the formation of pyrrolo[1,2-c]imidazole-6-carbonitriles, pyrrolo[1,2-с]imidazole-6-carboxylates and spiro[indoline-3,7'-pyrrolo[1,2-c]imidazoles], which can be considered as the analogues of both 3,3’-spirooxindole and 2-aminoimidazole marine sponge alkaloids.

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43

Yamuna, Thammarse S., Manpreet Kaur, Jerry P. Jasinski, Brian J. Anderson, and H. S. Yathirajan. "Two tautomers in the same crystal: 3-(4-fluorophenyl)-1H-pyrazole and 5-(4-fluorophenyl)-1H-pyrazole." Acta Crystallographica Section E Structure Reports Online 70, no. 9 (August 1, 2014): o949—o950. http://dx.doi.org/10.1107/s160053681401695x.

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The title co-crystal, 3-(4-fluorophenyl)-1H-pyrazole–5-(4-fluorophenyl)-1H-pyrazole (1/1), C9H7FN2, crystallizes with four independent molecules (A,B,CandD) in the asymmetric unit exhibiting two tautomeric forms (AandD;BandC) due to N—H proton exchange between the two N atoms of the pyrazole ring. The dihedral angles between the mean planes of the pyrazole and benzene rings are 15.6 (1), 19.8 (9), 14.0 (1) and 10.7 (7)° in moleculesA,B,CandD, respectively. In the crystal, N—H...N hydrogen bonds link the four molecules in the asymmetric unit into a ring with anR44(12) motif. Furthermore, weak C—H...F interactions link the molecules into a three-dimensional network.

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44

Narayana, B., Vinutha V. Salian, Balladka K. Sarojini, and Jerry P. Jasinski. "1-{3-(4-Chlorophenyl)-5-[4-(propan-2-yl)phenyl]-4,5-dihydro-1H-pyrazol-1-yl}butan-1-one." Acta Crystallographica Section E Structure Reports Online 70, no. 7 (June 11, 2014): o761—o762. http://dx.doi.org/10.1107/s1600536814013063.

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In the title compound, C22H25ClN2O, the pyrazole ring exhibits an envelope conformation with the methine C atom as the flap. The benzene rings are twisted by 3.3 (5) and 84.6 (5)° from the pyrazole mean plane, and are inclined to each other by 81.4 (4)°. In the crystal, pairs of weak C—H...O hydrogen bonds form centrosymmetric dimers with anR22(16) graph-set motif. C—H...π interactions link the dimers into columns propagating in [100].

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45

Sundaramoorthy, S., D. Gayathri, D. Velmurugan, K. Ravikumar, and M. Poornachandran. "3-(4-Methoxyphenyl)-6-(phenylsulfonyl)perhydro-1,3-thiazolo[3′,4′:1,2]pyrrolo[4,5-c]pyrrole." Acta Crystallographica Section E Structure Reports Online 64, no. 2 (January 25, 2008): o515. http://dx.doi.org/10.1107/s1600536808002134.

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46

Cristalli, G., P. Franchetti, M. Grifantini, E. Nasini, and S. Vittori. "SYNTHESIS OF 3- AND 4-CHLORO-1H-PYRROLO[3, 2-c]PYRIDIN-4(5H)-ONE." Organic Preparations and Procedures International 20, no. 3 (June 1988): 285–89. http://dx.doi.org/10.1080/00304948809355823.

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47

Suresh, J., R. Vishnupriya, S. Sivakumar, R. Ranjith Kumar, and S. Athimoolam. "Intermolecular C—H...O and C—H...Xinteractions in substituted spiroacenaphthylene structures." Acta Crystallographica Section C Crystal Structure Communications 68, no. 7 (June 13, 2012): o257—o261. http://dx.doi.org/10.1107/s0108270112024584.

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In the three spiroacenaphthylene structures 5′′-[(E)-2,3-dichlorobenzylidene]-7′-(2,3-dichlorophenyl)-1′′-methyldispiro[acenaphthylene-1,5′-pyrrolo[1,2-c][1,3]thiazole-6′,3′′-piperidine]-2,4′′-dione, C35H26Cl4N2O2S, (I), 5′′-[(E)-4-fluorobenzylidene]-7′-(4-fluorophenyl)-1′′-methyldispiro[acenaphthylene-1,5′-pyrrolo[1,2-c][1,3]thiazole-6′,3′′-piperidine]-2,4′′-dione, C35H28F2N2O2S, (II), and 5′′-[(E)-4-bromobenzylidene]-7′-(4-bromophenyl)-1′′-methyldispiro[acenaphthylene-1,5′-pyrrolo[1,2-c][1,3]thiazole-6′,3′′-piperidine]-2,4′′-dione, C35H28Br2N2O2S, (III), the substituted aryl groups are 2,3-dichloro-, 4-fluoro- and 4-bromophenyl, respectively. The six-membered piperidine ring in all three structures adopts a half-chair conformation, the thiazolidine ring adopts a slightly twisted envelope and the pyrrolidine ring an envelope conformation; in each case, the C atom linking the rings is the flap atom. In all three structures, weak intramolecular C—H...O interactions are present. The crystal packing is stabilized through a number of intermolecular C—H...O and C—H...Xinteractions, whereX= Cl in (I) and F or S in (II), and C—H...O interactions are observed predominantly in (III). In all three structures, molecules are linked through centrosymmetric ring motifs, further tailored through a relay of C—H...X[Cl in (I), Br in (II) and O in (III)] interactions.

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48

CAIRA, Mino R., Emilian GEORGESCU, Florentina GEORGESCU, and Florea DUMITRASCU. "Crystal Structure of Ethyl 3-(4-chlorobenzoyl)pyrrolo[1,2-c]quinazoline-1-carboxylate, a Pyrrolo[1,2-c]quinazoline Derivative." X-ray Structure Analysis Online 25 (2009): 5–6. http://dx.doi.org/10.2116/xraystruct.25.5.

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49

Sophy, Mohamed Ahmed Elian, and Mohamed Ahmed Mahmoud Abdel Reheim. "Synthesis of Some New 1, 3, 4-Oxadiazole, Pyrazole, and Pyrimidine Bearing Thienopyrazole Moieties." Current Organic Synthesis 17, no. 8 (October 28, 2020): 661–70. http://dx.doi.org/10.2174/1570179417999200730215318.

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Aim and Objective: According to the literature survey, pyrazole is a unique template that is associated with several biological activities. This article highlighted the research work of many researchers reported in the literature for synthesis and different pharmacological activities of the pyrazole nucleus. In the present work, pyrazol- 3-one 1 was reacted with cyanoacetic acid hydrazide and elemental sulfur to afford the corresponding thieno[3,2-c]pyrazol-6-carbohydrazide 3 derivatives. The latter compound reacted with some electrophilic reagents such as DMF-DMA, triethylorthoformate, arylidenemalononitriles and chalcones under neat conditions to give substituted oxadiazole and pyrazole, respectively. The treatment of compound 3 with active methylene reagents such as acetylacetone, diethylmalonate, ethyl acetoacetate and ethyl cyanoacetate under suitable conditions afforded pyrazole derivatives 10, 11, 13, and 15, respectively. Novel pyrazolothienopyrimidine 27 and 30 were prepared from precursor 26 with carbon disulfide and triethylorthoformate, respectively. The chemical structures of the newly synthesized compounds were established by elemental and spectral analyses including IR, and 1HNMR in addition to 13C-NMR and mass spectra. Materials and Methods: A novel substituted pyrazole, pyrimidine and pyrazolothienopyrimidine were obtained via Gewald synthesis of thiophene and fused thiophene and Mannich reactions of 5-amino-3-phenyl-1Hthieno[ 3,2-c]pyrazole-6-carbohydrazide. Results and Discussion: A series of some newly azoles and azines were prepared via reaction of thieno[3,2- c]pyrazol-6-carbohydrazide derivative 3 as starting material with some electrophilic and nucleophilic reagents. The structures of target compounds were established by elemental analyses and spectral data. Conclusion: Pyrazole is a unique template that is associated with several biological activities. This article highlighted the research work of many researchers reported in the literature for synthesis and different pharmacological activities of the pyrazole nucleus. In the current investigation, we have developed new and efficient methods for the synthesis of thieno[3,2-c]pyrazol-6-carbohydrazide derivatives. In addition, we have explored the preparative potential of these substances as intermediates for the synthesis of substituted pyrazoles and fused pyrazoles 10-30, respectively.

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50

Schönafinger, Karl, Christine M. Yasenchak, Anne Vollman, and Helen H. Ong. "Synthesis of 7,8,9,10-tetrahydropyrido[3′,4′:4,5]pyrrolo[2,3-c]quinolines." Journal of Heterocyclic Chemistry 25, no. 2 (March 1988): 535–37. http://dx.doi.org/10.1002/jhet.5570250233.

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