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Journal articles on the topic '2-d]pyrimidine'

Author: Grafiati

Published: 4 June 2021

Last updated: 16 February 2022

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1

SEELA, F., H. WINTER, and M. MOELLER. "ChemInform Abstract: Pyrazolo(3,4-d)pyrimidine 2′-Deoxy- and 2′,3′-Dideoxyribonucleosides: Glycosylation of 4-Methoxypyrazolo(3,4-d)pyrimidine." ChemInform 25, no. 19 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199419274.

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2

Stasevych, Maryna, Svitlana Sabat, Rostyslav Musyanovych, and Volodymyr Novikov. "Synthesis of condensed S-, N- containing heterocyclic systems on the base of 2-amino-4,9-dioxo-4,9-dihydronaphto[2,3-b]thiophene-3-ethylcarboxilate." Chemistry & Chemical Technology 2, no. 3 (September 15, 2008): 157–62. http://dx.doi.org/10.23939/chcht02.03.157.

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Synthesis of a new 2-aryl-4Н-naphtho[2’,3’,4,5]thieno[2,3-d][1,3]oxazine-4,5,10-triones, 2-arylnaphtho[2’,3’,4,5]thieno[2,3-d][1,3]pyrimidine-4,5,10(3Н)-triones, 3-phenyl naphtho[2’,3’,4,5]thieno[2,3-d][1,3]pyrimidine-2,4,5,10(1Н, 3Н)-tetraone and 2-thioxo-2,3-dyhydronaphth[2’,3’,4,5]thieno[2,3-d]pyrimidine-4,5,10(1Н)-trione was carried out. The mechanism of 2-aryl-4Н-naphtho[2’,3’,4,5]thieno[2,3-d][1,3]oxazine-4,5,10-triones formation was suggested.

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3

Azam, Mohammed Afzal, Loganathan Dharanya, Charu Chandrakant Mehta, and Sumit Sachdeva. "Synthesis and biological evaluation of some novel pyrazolopyrimidines incorporating a benzothiazole ring system." Acta Pharmaceutica 63, no. 1 (March 1, 2013): 19–30. http://dx.doi.org/10.2478/acph-2013-0001.

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In the present study, a series of benzothiazol derivatives 3a-l containing pyrazolo[3,4-d]pyrimidine moiety at the second position were synthesized and characterized by analytical and spectral data. The compounds were tested for their in vitro antimicrobial activity. Compounds 1-(1,3-benzothiazol-2- yl)-3-methyl-4-phenyl-1H-pyrazolo[3,4-d]pyrimidine (3a), 1- (1,3-benzothiazol-2-yl)-4-(4-chlorophenyl)-3-methyl-1H-pyrazolo[ 3,4-d]pyrimidine (3d) and 1-(1,3-benzothiazol-2-yl)- 3-methyl-4-substituted phenyl-1H-pyrazolo[3,4-d]pyrimidines (3h-j) showed significant inhibitory activity against P. aeruginosa whereas compounds 1-(1,3-benzothiazol-2-yl)-4- (2-chlorophenyl)-3-methyl-1H-pyrazolo[3,4-d]pyrimidine (3b), 2-[1-(1,3-benzothiazol-2-yl)-3-methyl-1H-pyrazolo[3,4-d]pyrimidin- 4-yl]phenol (3e), 1-(1,3-benzothiazol-2-yl)-4-(3,4-dimethoxyphenyl)- 3-methyl-1H-pyrazolo[3,4-d]pyrimidine (3h), 4-[1-(1,3-benzothiazol-2-yl)-3-methyl-1H-pyrazolo[3,4-d]pyri midin-4-yl]-N,N-dimethylaniline (3j) and 1-(1,3-benzothiazol- 2-yl)-3-methyl-4-[2-phenylvinyl]-1H-pyrazolo[3,4-d]pyrimidine (3k) were found to be active against C. albicans. Some of these synthesized compounds were evaluated for their in vivo acute toxicity, analgesic, anti-inflammatory, and ulcerogenic actions. The tested compound 4-[1-(1,3-benzothiazol- 2-yl)-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-N, N-dimethylaniline (3j) exhibited maximum analgesic and anti-inflammatory activities. Compounds 1-(1,3-benzothiazol- -2-yl)-3-methyl-4-(3-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidine (3i) and 3j showed a significant gastrointestinal protection compared to the standard drug diclofenac sodium.

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4

Seela, Frank, Holger Winter, and Marianne Möller. "Pyrazolo[3,4-d]pyrimidine 2′ -Deoxy- and 2′,3′ -Dideoxyribonucleosides: Studies on the glycosylation of 4-methoxypyrazolo[3,4-d]pyrimidine." Helvetica Chimica Acta 76, no. 4 (June 30, 1993): 1450–58. http://dx.doi.org/10.1002/hlca.19930760405.

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5

Yokota, Kenichirou, Masayori Hagimori, Naoko Mizuyama, Yasuhisa Nishimura, Hiroshi Fujito, Yasuhiro Shigemitsu, and Yoshinori Tominaga. "Synthesis, solid-state fluorescence properties, and computational analysis of novel 2-aminobenzo[4,5]thieno[3,2-d]pyrimidine 5,5-dioxides." Beilstein Journal of Organic Chemistry 8 (February 16, 2012): 266–74. http://dx.doi.org/10.3762/bjoc.8.28.

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New fluorescent compounds, benzo[4,5]thieno[3,2-d]pyrimidine 5,5-dioxides (3a–g), 2-amino-4-methylsulfanylbenzo[4,5]thieno[3,2-d]pyrimidine (6), and 2-amino-4-methylsulfanyl-7-methoxybenzo[4,5]furo[3,2-d]pyrimidine (7), were synthesized in good yields from heterocyclic ketene dithioacetals (1a–c) and guanidine carbonate (2a) or (S)-methylisothiourea sulfate (2b) in pyridine under reflux. Among the fused pyrimidine derivatives, compound 3c, which has an amino group at the 2-position and a benzylamino group at the 4-position of the pyrimidine ring, showed the strongest solid-state fluorescence. The absorption and emission properties of the compounds were quantitatively reproduced by a series of ab initio quantum-chemical calculations.

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6

Hossain, M. I., and M. M. H. Bhuiyan. "Synthesis and Antimicrobial Activities of Some New Thieno and Furopyrimidine Derivatives." Journal of Scientific Research 1, no. 2 (April 23, 2009): 317–25. http://dx.doi.org/10.3329/jsr.v1i2.2299.

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Fused pyrimidines, 8,9-dimethyl[1,2,4]triazolo[4,3-c]thieno[3,2-e]pyrimidine 5, 3,8,9-trimethyl[1,2,4]triazolo[4,3-c]thieno[3,2-e]pyrimidine 6, 4-benzylidinehydrazono-5,6 dimethylthieno[2,3-d]pyrimidine 7, 4-[4/-hydroxybenzylidine]hydrazono-5,6-dimethylthi-eno[2,3-d]pyrimidine 8, 4-[4/-tolylidin]hydrazono-5,6-dimethylthieno[2,3-d]pyrimidine 9, 4-[4/-nitrobenzylidine]hydrazono-5-ethyl-6-methylthieno[2,3-d]pyrimidine 10 and 4-[4/-chlorobenzylidine]hydrazono-5-ethyl-6-methylthieno[2,3-d]pyrimidine 11 are prepared in good yield by an initial treatment of 2-amino-4,5-dimethylthiophene-3-carbonitrile 1 with formic acid, affording 5,6-dimethylthieno[2,3-d]pyrimidin-4(3H)-one 2, which is chlorinated with thionyl chloride and then hydrazinated with hydrazine hydrate. Finally hydrazino compound 4 is reacted with formic acid, acetic anhydrate, benzaldehyde, p-hydroxybenzaldehyde, p-toluayldehyde, p-nitrobenzaldehyde and p-chlorobenzaldehyde to give thienotriazolopyrimidines 5-6 and thienopyrimidines 7-11 respectively. All the compounds have been screened for their antimicrobial activity. Keywords: Fused pyrimidines; Hydrazino compound; Thienotriazolopyrmidines; Thienopyrimidines; Antimicrobial activity.© 2009 JSR Publications. ISSN: 2070-0237 (Print); 2070-0245 (Online). All rights reserved.DOI: 10.3329/jsr.v1i2.2299

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7

Kobayashi, Kazuhiro, Ippei Nozawa, Hiroaki Utsumi, Takuma Ueyama, Hidetaka Hiyoshi, and Kazuto Umezu. "Synthesis of 7,8-Dihydropyrido[2,3-d]pyrimidine Derivatives from 4,6-Dichloro-2-(methylsulfanyl)pyrimidine." HETEROCYCLES 94, no. 8 (2017): 1427. http://dx.doi.org/10.3987/com-17-13720.

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8

Subbagh, Hussein I. El, Li-Jen Ping, and Elie Abushanab. "A Stereospecific Synthesis of Pyrimidine β-D-2′-Deoxyribonucleosides." Nucleosides and Nucleotides 11, no. 2-4 (February 1992): 603–13. http://dx.doi.org/10.1080/07328319208021729.

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9

Vicentes, Daniel E., Ricaurte Rodríguez, Patricia Ochoa, Justo Cobo, and Christopher Glidewell. "A concise and efficient synthesis of amino-substituted (1H-benzo[d]imidazol-1-yl)pyrimidine hybrids: synthetic sequence and the molecular and supramolecular structures of six examples." Acta Crystallographica Section C Structural Chemistry 75, no. 10 (September 25, 2019): 1405–16. http://dx.doi.org/10.1107/s2053229619012087.

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A concise and efficient synthesis of a series of amino-substituted benzimidazole–pyrimidine hybrids has been developed, starting from the readily available N 4-(2-aminophenyl)-6-methoxy-5-nitrosopyrimidine-2,4-diamine. In each of N 5-benzyl-6-methoxy-4-(2-phenyl-1H-benzo[d]imidazol-1-yl)pyrimidine-2,5-diamine, C25H22N6O, (I), 6-methoxy-N 5-(4-methoxybenzyl)-4-[2-(4-methoxyphenyl)-1H-benzo[d]imidazol-1-yl]pyrimidine-2,5-diamine, C27H26N6O3, (III), 6-methoxy-N 5-(4-nitrobenzyl)-4-[2-(4-nitrophenyl)-1H-benzo[d]imidazol-1-yl]pyrimidine-2,5-diamine, C25H20N8O5, (IV), the molecules are linked into three-dimensional framework structures, using different combinations of N—H...N, N—H...O, C—H...O, C—H...N and C—H...π hydrogen bonds in each case. Oxidative cleavage of 6-methoxy-N 5-(4-methylbenzyl)-4-[2-(4-methylphenyl)-1H-benzo[d]imidazol-1-yl]pyrimidine-2,5-diamine, (II), with diiodine gave 6-methoxy-4-[2-(4-methylphenyl)-1H-benzo[d]imidazol-1-yl]pyrimidine-2,5-diamine, which crystallized as a monohydrate, C19H18N6O·H2O, (V), and reaction of (V) with trifluoroacetic acid gave two isomeric products, namely N-{5-amino-6-methoxy-6-[2-(4-methylphenyl)-1H-benzo[d]imidazol-1-yl]pyrimidin-2-yl}-2,2,2-trifluoroacetamide, which crystallized as an ethyl acetate monosolvate, C21H17F3N6O2·C4H8O2, (VI), and N-{2-amino-6-methoxy-4-[2-(4-methylphenyl)-1H-benzo[d]imidazol-1-yl]pyrimidin-5-yl}-2,2,2-trifluoroacetamide, which crystallized as a methanol monosolvate, C21H17F3N6O2·CH4O, (VIIa). For each of (V), (VI) and (VIIa), the supramolecular assembly is two-dimensional, based on different combinations of O—H...N, N—H...O, N—H...N, C—H...O and C—H...π hydrogen bonds in each case. Comparisons are made with some related structures.

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10

Tiwari, Sangeeta, Ashok K. Yadav, and A. K. Mishra. "Some New Pyrido[2,3-d]pyridimines and their Nucleoside of Biological Importance." E-Journal of Chemistry 7, s1 (2010): S85—S92. http://dx.doi.org/10.1155/2010/812567.

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Chalcones (I) reacted with malanonitrile and ammonium acetate yielded 2-amino-3-cyano-4,6-disubstituted pyridines (II) in excellent yield. 4-Amino-5,7-disubstituted pyrido [2,3-d]pyrimidine-2(1H)-thiones (III), 4-amino-5,7-disubstituted pyrido[2,3-d]pyrimidines (IV) and 4-imino-3,5,7-trisubstituted pyrido[2,3-d]pyrimidin-2(1H)-ones (V) have been synthesized by the condensation of compound (II) with thiourea, formamide and arylisocynate respectively. The ribofuranosidesviz. 4-amino-5,7-disubstituted-1- [2',3',5'-tri-o-benzoyl-β,D-ribofuranosyl]pyrido[2,3-d]pyrimidine-2-(1H)-thiones (VI) and 4-imino-3,5,7- trisubstituted-1- [2',3',5'-tri-o-benzoyl-β,D-ribofuranosyl] pyrido [2,3-d] pyrimidine-2(1H)-one (VII) were synthesized by converting compounds III and V to trimethylsilyl derivative in situ by reacting them with hexamethyldisilazane to give corresponding ribofuranosides withβ-D-ribofuranose-1-acetate-2,3,5-tribenzoate. Compounds III-V and their ribofuranosides have been screened for antimicrobial and antifungal evaluations.

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11

Mamaghani, Manouchehr. "Ultrasound-promoted synthesis of novel dihydropyrido[2,3-d:5,6- d`]dipyrimidine derivatives." JOURNAL OF ADVANCES IN CHEMISTRY 11, no. 5 (April 18, 2015): 3567–75. http://dx.doi.org/10.24297/jac.v11i5.4475.

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An efficient synthesis of dihydropyrido[2,3-d:5,6-d`]pyrimidine derivatives was developed via one-pot three-component reaction of 6-amino-2-(alkylthio)-pyrimidine-4(3H)one and aryl aldehydes in the mixed solvent of glacial acetic acid and DMF (1:1, v:v) under ultrasonic irradiation. In this protocol novel fused dihydropyrido[2,3-d]pyrimidines were synthesized in high yields (80-97%) and lower reaction times (5-25 min).

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12

Bakhite, E. A., A. E. Abdel-Rahman, O. S. Mohamed, and E. A. Thabet. "synthesis of Some New Pyridothienopyrimidines and Related [1,2,4]Triazolopyridothienopyrimidines." Journal of Chemical Research 2003, no. 2 (January 2003): 58–59. http://dx.doi.org/10.3184/030823403103173156.

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4-Chloro-9-phenyl-7-(2-thienyl)pyrido[3′,2′:4,5]thieno[3,2- d]pyrimidine (5) and 3-amino-3,4-dihydro-4-imino-9-phenyl-7-(2-thienyl)pyrido[3′,2′:4,5]thieno[3,2- d]pyrimidine (19) were prepared and employed as precursors for synthesizing the fused-ring compounds of the title.

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13

Abdel-Hafez, Shams H., Ragaa A. Ahmed, Mohamed A. Abdel-Azim, and Khairy M. Hassan. "Selenium containing Heterocycles: Part 1. Synthesis of Some New Substituted Pyrido[3′,2′:4,5]selenolo[3,2-d]pyrimidines and Related Fused Tetracyclic Systems." Journal of Chemical Research 2007, no. 10 (October 2007): 580–84. http://dx.doi.org/10.3184/030823407x25506.

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New series of selenolo[2,3- b]pyridine, pyrido[3′,2′:4,5]selenolo[3,2- d]pyrimidine, 7,8-dihydro-2,4-dimethylpyrrolo [1,2- a]pyrido[3′,2′:4,5]selenolo[3,2- d]pyrimidin-10(6 H)-one and 7,9-dimethylpyrido[3′,2′:4,5]selenolo[3,2- d][1,2,4] triazolo[4,3- c]pyrimidine derivatives were synthesised from 3-cyano-4,6-dimethylpyridine-2(1 H)-selenone (1). Spectroscopic (IR, 1H, MS) of the newly synthesised compounds are reported.

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14

Hashmi, Imran Ali, Holger Feist, Manfred Michalik, Helmut Reinke, and Klaus Peseke. "Dimethylaminomethylene-α-D-xylo-hept-5-ulofuranurononitrile as Building Block in the Synthesis of ‘Reversed’ C-Nucleoside Analogues." Zeitschrift für Naturforschung B 61, no. 3 (March 1, 2006): 292–300. http://dx.doi.org/10.1515/znb-2006-0309.

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Abstract 3-O-Benzyl-6-deoxy-1,2-O-isopropylidene-6-(dimethylaminomethylene)-α-D-xylo-hept-5-ulofuranurononitrile (1) was reacted with amidinium salts, S-methylisothiouronium sulfate, and guanidinium chloride, respectively, in the presence of bases to furnish the 4-(3-O-benzyl-1,2-O-isopropylidene- α-D-xylo-tetrofuranos-4-yl)pyrimidine-5-carbonitriles 2 and the 4-(1,2-O-isopropylidene- α-D-glycero-tetr-3-enofuranos-4-yl)pyrimidine-5-carbonitriles 3, respectively. Treatment of 1 with ethyl 5-aminopyrazole-4-carboxylates yielded the ethyl 7-(3-O-benzyl-1,2-O-isopropylidene- α-D-xylo-tetrofuranos-4-yl)-6-cyanopyrazolo[1,5-a]pyrimidine-3-carboxylates 4 and the ethyl 7-amino-6-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-pentofuranuronoyl)pyrazolo[1,5-a]pyrimidine- 3-carboxylates 5, respectively. Reaction of 1 with 2-benzimidazolylacetonitrile in the presence of sodium methanolate afforded 1-amino-2-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-pentofuranuronoyl) benzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile (6) and 1-amino-2-(3-deoxy-1,2-O-isopropylidene- α-D-glycero-pent-3-enofuranuronoyl)benzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile (7).

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15

Singh, Shiv Dev, Arvind Kumar, Firoz Babar, Neetu Sachan, and Arun Kumar Sharma. "Synthesis of Novel 3(N,N-dialkylamino)alkyl/phenyl Substituted Thieno [2,3-d]pyrimidinones as H1-Anti-Histaminic and Antimicrobial Agents." Current Bioactive Compounds 15, no. 1 (February 6, 2019): 63–70. http://dx.doi.org/10.2174/1573407214666180226130957.

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Background: Thienopyrimidines are the bioisoster of quinazoline and unlike quinazoline exist in three isomeric forms corresponding to the three possible types annulation of thiophene to the pyrimidine ring viz thieno[2,3-d] pyrimidine, thieno[3,2-d] pyrimidine and thieno[3,4-d]pyrimidine. Heterocyclic containing the thienopyrimidinone moiety exhibits various pronounced activities such as anti-hypertensive, analgesic and anti-inflammatory, antiviral, platelet aggregation inhibitory, antiprotozoal bronchodilatory, phosphodiesterase inhibitory, antihistaminic, antipsychotic and antimicrobial activity. Objective: Synthesis of novel 3(N,N-dialkylamino)alkyl/phenyl substituted thieno[2,3-d]pyrimidinones as H1-anti-histaminic and antimicrobial agents. Methods: A series of 3-[(N,N-dialkylamino)alkyl/phenyl]-2-(1H)thioxo-5,6,7,8-tetrahydrobenzo(b) thieno(2,3-d)pyrimidine-4(3H)-ones[4a-d], their oxo analogous [5a-d] and 3-[(N,N-dialkylamino)alkyl]- 2-chlorophenyl-5,6,7,8-tetrahydrobenzo(b)thieno(2,3-d)pyrimidine- 4 (3H)-ones[6a-d]derivative were synthesized from 2-amino-4,5,6,7-tetrahydrobenzo(b)thiophene-3-carboxylic acid by nucleophilic substitution of different N,N-dialkyl alkylene/phenylene diamines on activated 3-acylchloride moiety followed by cyclocondensation with carbon disulfide and ethanolic potassium hydroxide to get [4a-d] and in second reaction by condensation with 4-chlorobenzoyl chloride to get [6a-d] by single pot novel innovative route. The oxo analogous [5a-d] were prepared by treating derivatives [4a-d] with potassium permagnate in ethanolic KOH. The synthesized compound were evaluated for H1-antihistaminic and antimicrobial activities. Results: All synthesized compounds exhibited significant H1-antihistaminic activity by in vitro and in vivo screening methods and data were verified analytically and statistically. The compound 4a, 4b, 5a and 5b showed significant H1-antihistaminiic activity than the reference standard chlorpheniramine maleate. The compound 6d, 6c, 5c and 4c exhibited significant antimicrobial activity.

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16

KONNO, Shoetsu, Ryo WATANABE, and Hiroshi YAMANAKA. "Studies on Pyrimidine Derivatives. XLII. Reactivity of 4-Methyl Group of 2, 4-Dimethylthieno [2, 3-d] pyrimidine." YAKUGAKU ZASSHI 109, no. 9 (1989): 642–49. http://dx.doi.org/10.1248/yakushi1947.109.9_642.

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17

Otero, Iran, Holger Feist, Dirk Michalik, Manfred Michalik, José Quincoces, and Klaus Peseke. "Synthesis of Iso-C-nucleoside Analogues from 1-(Methyl 2-O-benzyl-4,6- O-benzylidene-3-deoxy-α-D-altropyranosid-3-yl)but-3-yn-2-ones." Zeitschrift für Naturforschung B 60, no. 11 (November 1, 2005): 1175–85. http://dx.doi.org/10.1515/znb-2005-1110.

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1-(Methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-D-altropyranosid-3-yl)but-3-yn-2-one (3a) reacted with 3-amino-1H-1,2,4-triazole and 5-aminopyrazole-4-carboxylic acid derivatives in the presence of base to furnish the triazolo[1,5-a]pyrimidine (5) and the pyrazolo[1,5- a]pyrimidines (8a - d), respectively. Treatment of 1-(methyl 2-O-benzyl-4,6-O-benzylidene-3- deoxy-α-D-altropyranosid-3-yl)-4-phenyl-but-3-yn-2-one (3b) with cyanacetamide, 2-cyano-N- (4-methoxyphenyl)acetamide und N-aryl-3-oxo-butyramides afforded the substituted nicotinonitriles (11a - d). Furthermore, reaction of 3b with 2-benzimidazolyl-acetonitrile yielded the benz[4,5]imidazo[1,2-a]pyridine-4-carbonitrile (13). Deprotection of 8d in two steps afforded the 2-amino-N-benzyl-5-(methyl 3-deoxy-α-D-altropyranosid-3-yl-methyl)pyrazolo[1,5-a]pyrimidine- 3-carboxamide (10). Compounds 5 and 11d were treated with AcOH/H2O to furnish the 5-(methyl 2-O-benzyl-3-deoxy-α-D-altropyranosid-3-yl-methyl)[1,2,4]triazolo[1,5-a]pyrimidine (6) and the 3-acetyl-1,2-dihydro-1-(4-methoxyphenyl)-6-(methyl 2-O-benzyl-3-deoxy-α-D-altropyranosid-3-ylmethyl)- 4-phenylpyridin-2-one (12), respectively.

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18

Jubete, Guillem, Raimon Puig de la Bellacasa, Roger Estrada-Tejedor, Jordi Teixidó, and José I. Borrell. "Pyrido[2,3-d]pyrimidin-7(8H)-ones: Synthesis and Biomedical Applications." Molecules 24, no. 22 (November 16, 2019): 4161. http://dx.doi.org/10.3390/molecules24224161.

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Pyrido[2,3-d]pyrimidines (1) are a type of privileged heterocyclic scaffolds capable of providing ligands for several receptors in the body. Among such structures, our group and others have been particularly interested in pyrido[2,3-d]pyrimidine-7(8H)-ones (2) due to the similitude with nitrogen bases present in DNA and RNA. Currently there are more than 20,000 structures 2 described which correspond to around 2900 references (half of them being patents). Furthermore, the number of references containing compounds of general structure 2 have increased almost exponentially in the last 10 years. The present review covers the synthetic methods used for the synthesis of pyrido[2,3-d]pyrimidine-7(8H)-ones (2), both starting from a preformed pyrimidine ring or a pyridine ring, and the biomedical applications of such compounds.

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19

Votruba, Ivan, Antonín Holý, Hana Dvořáková, Jaroslav Günter, Dana Hocková, Hubert Hřebabecký, Tomas Cihlar, and Milena Masojídková. "Synthesis of 2-Deoxy-β-D-ribonucleosides and 2,3-Dideoxy-β-D-pentofuranosides on Immobilized Bacterial Cells." Collection of Czechoslovak Chemical Communications 59, no. 10 (1994): 2303–30. http://dx.doi.org/10.1135/cccc19942303.

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Alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli catalyze the transfer of 2-deoxy-D-ribofuranosyl moiety of 2'-deoxyuridine to purine and pyrimidine bases as well as their aza and deaza analogs. All experiments invariably gave β-anomers; in most cases, the reaction was regiospecific, affording N9-isomers in the purine and N1-isomers in the pyrimidine series. Also a 2,3-dideoxynucleoside can serve as donor of the glycosyl moiety. The acceptor activity of purine bases depends only little on substitution, the only condition being the presence of N7-nitrogen atom. On the other hand, in the pyrimidine series the activity is limited to only a narrow choice of mostly short 5-alkyl and 5-halogeno uracil derivatives. Heterocyclic bases containing amino groups are deaminated; this can be avoided by conversion of the base to the corresponding N-dimethylaminomethylene derivative which is then ammonolyzed. The method was verified by isolation of 9-(2-deoxy-β-D-ribofuranosyl) derivatives of adenine, guanine, 2-chloroadenine, 6-methylpurine, 8-azaadenine, 8-azaguanine, 1-deazaadenine, 3-deazaadenine, 1-(2-deoxy-β-D-ribofuranosyl) derivatives of 5-ethyluracil, 5-fluorouracil, and 9-(2,3-dideoxy-β-D-pentofuranosyl)hypoxanthine, 9-(2,3-dideoxy-β-D-pentofuranosyl)-6-methylpurine, and other nucleosides.

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20

Zhou, Zhihui, Caolin Wang, Zhen Xiao, Qi Yang, and Shan Xu. "Synthesis of 2-chloro-4-(3-nitrophenoxy) thieno [3, 2-d] pyrimidine." IOP Conference Series: Earth and Environmental Science 252 (July 9, 2019): 022091. http://dx.doi.org/10.1088/1755-1315/252/2/022091.

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21

Seela, Frank, and Heinz-Peter Muth. "Synthesis of 4-substituted 2-aminopyrrolo[2,3-d]pyrimidine 2′,3′-dideoxyribonucleosides." Liebigs Annalen der Chemie 1990, no. 3 (March 12, 1990): 227–32. http://dx.doi.org/10.1002/jlac.199019900141.

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22

Gainsford, Graeme J., and Gary B. Evans. "3-Bromo-7-methoxy-2-(tetrahydropyran-2-yl)pyrazolo[4,3-d]pyrimidine." Acta Crystallographica Section E Structure Reports Online 58, no. 9 (August 23, 2002): o1021—o1022. http://dx.doi.org/10.1107/s1600536802014988.

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23

Borrell, José I., Jordi Teixidó, Blanca Martínez-Teipel, Blanca Serra, Josep Lluís Matallana, Marta Costa, and Xavier Batllori. "An Unequivocal Synthesis of 4-Amino-1,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-2,7-diones and 2-Amino-3,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-4,7-diones." Collection of Czechoslovak Chemical Communications 61, no. 6 (1996): 901–9. http://dx.doi.org/10.1135/cccc19960901.

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An unequivocal set of procedures for the synthesis of 4-amino-1,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-2,7-diones (7) and 2-amino-3,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-4,7-diones (8), in a maximum of four steps from an α,β-unsaturated ester 1, is reported. Thus, the acid hydrolysis of the 2,4-diaminopyrido[2,3-d]pyrimidines 3 yields the 4-amino-2-oxopyrido[2,3-d]pyrimidines 7 while the cyclization of the Michael adducts 9 (formed by reaction of 1 and methyl cyanoacetate) with guanidine affords the corresponding 2-amino-4-oxopyrido[2,3-d]pyrimidines 8. Both isomers were also obtained by hydrolysis of the 4-amino-2-bromo- and 2-amino-4-bromo-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-ones 5 and 6, respectively.

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24

Biswas, G., T. Chandra, N. Garg, D. S. Bhakuni, A. Pramanik, K. Avasthi, and P. R. Maulik. "A [3.1.0]-Fused 2',3'-Modified β-D-Pyrazolo[3,4-d]pyrimidine Nucleoside." Acta Crystallographica Section C Crystal Structure Communications 52, no. 10 (October 15, 1996): 2563–66. http://dx.doi.org/10.1107/s0108270196004015.

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25

Oertel, Frank, Holger Winter, Zygmunt Kazimierczuk, J. A. Vilpo, Peter Richter, and Frank Seela. "Synthesis and Properties of Methylthiopyrazolo[3,4-d]pyrimidine 2′-Deoxy-β-D-ribonucleosides." Liebigs Annalen der Chemie 1992, no. 11 (November 20, 1992): 1165–70. http://dx.doi.org/10.1002/jlac.1992199201191.

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26

Shortnacy-Fowler, Anita T, Kamal N Tiwari, John A Montgomery, Robert W Buckheit, Jr., John A Secrist III, and Frank Seela. "Synthesis and Biological Activity of 2′-Fluoro-D-arabinofuranosylpyrazolo[3,4-d]pyrimidine Nucleosides." Helvetica Chimica Acta 82, no. 12 (December 15, 1999): 2240–45. http://dx.doi.org/10.1002/(sici)1522-2675(19991215)82:12<2240::aid-hlca2240>3.0.co;2-2.

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27

Muzychka, Lyubov, Iryna Yaremchuk, Iryna Yaremchuk, and Oleg Smolii. "7-Substituted pyrrolo[2,3-d]pyrimidines for the synthesis of new 1-deazapyrimido[1,2,3-cd]purines." French-Ukrainian Journal of Chemistry 5, no. 2 (2017): 15–23. http://dx.doi.org/10.17721/fujcv5i2p15-23.

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Few examples of new heterocyclic 1-deazapyrimido[1,2,3-cd]purine derivatives were synthesized by intramolecular cyclization of methyl 7-(oxiran-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylates. The latter were obtained by iodolactonization of 7-allylpyrrolo[2,3-d]pyrimidine-6-carboxylic acids.

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28

Sirakanyan, Spinelli, Geronikaki, Hakobyan, Sahakyan, Arabyan, Zakaryan, et al. "Synthesis, Antitumor Activity, and Docking Analysis of New Pyrido[3’,2’:4,5]furo(thieno)[3,2-d]pyrimidin-8-amines." Molecules 24, no. 21 (October 31, 2019): 3952. http://dx.doi.org/10.3390/molecules24213952.

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Continuing our research in the field of new heterocyclic compounds, herein we report on the synthesis and antitumor activity of new amino derivatives of pyrido[3’,2’:4,5](furo)thieno[3,2-d]pyrimidines as well as of two new heterocyclic systems: furo[2–e]imidazo[1,2-c]pyrimidine and furo[2,3-e]pyrimido[1,2-c]pyrimidine. Thus, by refluxing the 8-chloro derivatives of pyrido[3’,2’:4,5]thieno(furo)[3,2-d]pyrimidines with various amines, the relevant pyrido[3’,2’:4,5]thieno(furo)[3,2-d]pyrimidin-8-amines were obtained. Further, the cyclization of some amines under the action of phosphorus oxychloride led to the formation of new heterorings: imidazo[1,2-c]pyrimidine and pyrimido[1,2-c]pyrimidine. The possible antitumor activity of the newly synthesized compounds was evaluated in vitro. The biological tests evidenced that some of them showed pronounced antitumor activity. A study of the structure–activity relationships revealed that the compound activity depended mostly on the nature of the amine fragments. A docking analysis was also performed for the most active compounds.

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29

Trilleras, Jorge, Jairo Quiroga, Justo Cobo, Antonio Marchal, Manuel Nogueras, John N. Low, and Christopher Glidewell. "Anhydrous versus hydrated N 4-substituted 1H-pyrazolo[3,4-d]pyrimidine-4,6-diamines: hydrogen bonding in two and three dimensions." Acta Crystallographica Section B Structural Science 64, no. 5 (September 15, 2008): 610–22. http://dx.doi.org/10.1107/s0108768108019903.

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Ten new N 4-substituted 1H-pyrazolo[3,4-d]pyrimidine-4,6-diamines have been synthesized and the structures of nine of them are reported here, falling into two clear groups, those which are stoichiometric hydrates and those which crystallize in solvent-free forms. In each of N 4-methyl-N 4-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine, C12H12N6 (I), N 4-cyclohexyl-N 4-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine, C12H18N6 (II), and N 4-(3-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine, C11H9ClN6 (III), the molecules are linked into hydrogen-bonded sheets. The molecules of 2-{4-(6-amino-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl}ethanol, C11H17N7O (IV), are linked into a three-dimensional framework, while the structure of N 4-methyl-N 4-(4-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine monohydrate, C13H14N6·H2O (V), is only two-dimensional despite the presence of five independent hydrogen bonds. The stoichiometric hemihydrates N 4-ethyl-N 4-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine hemihydrate, C13H14N6·0.5H2O (VI) and N 4-(4-methoxyphenyl)-N 4-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine hemihydrate, C13H14N6O·0.5H2O (VII), exhibit remarkably similar sheet structures, despite different space groups and Z′ values, Z′ = 0.5 in C2/c for (VI) and Z′ = 1 in P\bar 1 for (VII). N 4-4-Benzyl-N 4-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine monohydrate, C18H16N6·H2O (VIII), crystallizes with Z′ = 2 in P21/n, and the four independent molecular components are linked into sheets by a total of 11 intermolecular hydrogen bonds. The sheet structure in {4-(pyrrolidin-1-yl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine} ethanol hemisolvate hemihydrate, C9H12N6·0.5C2H6O·0.5H2O (IX), is built from the pyrimidine and water components only; it contains eight independent hydrogen bonds, and it very closely mimics the sheets in (VI) and (VII); the ethanol molecules are pendent from these sheets. The N 4-alkyl-N 4-aryl-4-aminopyrazolopyrimidine molecules in (I), (V)–(VIII) all adopt very similar conformations, dominated in each case by an intramolecular C—H...π(arene) hydrogen bond: this interaction is absent from (III) where the molecular conformation is entirely different and probably dominated by the intermolecular hydrogen bonds.

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30

Tsiveriotis, P., N. Hadjiliadis, F. Dahan, and J. P. Laussac. "Methyl 4-Diethylamino-2-formamidothieno[2,3-d]pyrimidine-6-carboxylate." Acta Crystallographica Section C Crystal Structure Communications 51, no. 8 (August 15, 1995): 1607–9. http://dx.doi.org/10.1107/s0108270194012692.

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31

Seela, Frank, Xin Ming, Simone Budow, Henning Eickmeier, and Hans Reuter. "2′-Deoxyimmunosine: a thiazolo[4,5-d]pyrimidine nucleoside adopting thesynconformation." Acta Crystallographica Section C Crystal Structure Communications 63, no. 9 (August 17, 2007): o549—o551. http://dx.doi.org/10.1107/s010827010703750x.

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32

Tinant, B., J. P. Declercq, J. P. Bouillon, and H. G. Viehe. "CRYSTAL STRUCTURE OF 2-PHENYL-6-TRIFLUOROMETHYL-DIHYDROCYCLOPENTA[d]PYRIMIDINE." Bulletin des Sociétés Chimiques Belges 103, no. 11 (September 1, 2010): 695–96. http://dx.doi.org/10.1002/bscb.19941031112.

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33

Behera, Manoranjan, M. Sambaiah, Poosa Mallesham, K. Shiva Kumar, Yamini Bobde, Prasanta Hota, Satyanarayana Yennam, and Balaram Ghosh. "Tandem Schiff-Base Formation/Heterocyclization: An Approach to the Synthesis of Fused Pyrazolo–Pyrimidine/Isoxazolo-Pyrimidine Hybrids." Synlett 30, no. 05 (February 5, 2019): 586–92. http://dx.doi.org/10.1055/s-0037-1612081.

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A new synthesis of pyrazolo[4,3-d]pyrimidines and isoxazolo[4,5-d]pyrimidines is described. Key steps in the synthesis involve Stille coupling of 4,6-dichloro-2-phenyl-pyrimidine with tributyl(1-ethoxyvinyl)stannane and tandem Schiff-base formation/heterocyclization of 2,6-di-aryl-5-fluoro-4-acetylpyrimidine with hydrazines or hydroxylamine to give pyrazolo[4,3-d]pyrimidines and isoxazolo[4,5-d]pyrimidines, respectively. The position of the fluoro group in the pyrimidine ring is important for the success of heterocylization reaction.

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34

Edrees, Mastoura M. "Synthesis of 4-hydrazinopyrazolo[3,4-d]pyrimidines and their Reactions with Carbonyl Compounds." Journal of Chemical Research 37, no. 1 (January 2013): 6–10. http://dx.doi.org/10.3184/174751912x13543818811749.

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Synthesis of a new 4-hydrazinopyrazolo[3,4- d]pyrimidine was achieved via heating (4,6-dithioxo-1 H-pyrazolo[3,4- d] pyrimidin-3-yl)acetonitrile with hydrazine hydrate. Reactions of the latter product with thiophene-2-carbaldehyde and ethyl hydrazonoacetoacetate analogues afforded the corresponding hydrazone and pyrazole derivatives, respectively. Similarly, condensation of 2-[6-(benzylsulfanyl)-4-hydrazino-1 H-pyrazolo[3,4- d]pyrimidin-3-yl]acetonitrile with thiophene-2-carbaldehyde and ethyl hydrazonoacetoacetate analogues gave the respective hydrazone and pyrazolone derivatives. Alkylation reactions of 2-[4,6-bis(benzylsulfanyl)-1 H-pyrazolo[3,4- d]pyrimidin-3-yl]acetonitrile with arylamines gave the respective 4-( N-arylamino)-6-benzylsulfanylpyrazolo[3,4- d]pyrimidine derivatives.

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35

Swelam, Samira, Abd El-Salam, and Magdi Zaki. "Synthesis of some pyrazolo[3,4-d]pyrimidines and their fused triazole and tetrazole derivatives." Journal of the Serbian Chemical Society 64, no. 11 (1999): 655–62. http://dx.doi.org/10.2298/jsc9911655s.

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Reaction of 2 with different reagents, namely formic acid, acetic anhydride and trichloroacetonitrile, yielded pyrazolo[3,4-d]pyrimidine derivatives 3, 5 and 6, respectively. Pyrazolo[3,4-d]pyrimidine m-thiazine(7) and 2,4-(1H,3H)dithione (8) derivatives were formed by the action of carbon disulfide on 2, depending on the reaction medium. Interaction of 7 with hydrazine hydrate yielded the aminoimino derivative 9 which reacted with acetic anhydride, triethyl orthoacetate and/or appropriate aldehydes to give 11, 12 and 13a,b, respectively. Methylation of compound 8 gave 14, which reacted with hydrazine hydrate to afford the monohydrazino derivative 15. Reaction of 15, with formic acid and nitrous acid afforded pyrazolo[4,3-e]triazolo[1,5-c]pyrimidine (16) and pyrazolo[4,3-e]tetrazolo-[1,5-c]pyrimidine (17) derivatives, respectively. The structures of products 3-17 were identified in light of their elemental analyses and spectra data.

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36

Ahmed, Essam K., Johannes Fröhlich, and Fritz Sauter. "Fusion Reactions of N-Heterocyclic Moieties to Thiopyrano[4',3':4,5]thieno[2,3-d]pyrimidines." Collection of Czechoslovak Chemical Communications 61, no. 1 (1996): 147–54. http://dx.doi.org/10.1135/cccc19960147.

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Derivatives of the novel heterocyclic parent systems imidazolo[1,2-a]thiopyrano[4',3':4,5]thieno[2,3-d]pyrimidine (B) and thiopyrano[4',3':4,5]thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine (C) have been synthesized by fusing pyrimidine moieties to 2-amino-4,7-dihydro-5H-thieno[2,3-c]thiopyran-3-carboxylic acid ethyl ester (1) and -3-carbonitrile (10), followed by cyclization reactions of the title intermediates A thus obtained.

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37

Seela, Frank, and Sigrid Lampe. "8-Aza-2?-deoxyguanosine and Related 1,2,3-Triazolo[4,5-d]pyrimidine 2?-Deoxyribofuranosides." Helvetica Chimica Acta 76, no. 6 (September 22, 1993): 2388–97. http://dx.doi.org/10.1002/hlca.19930760625.

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38

Gurenko, A. O., O. V. Shablykin, and V. S. Brovarets. "Synthesis of 2-aryl-6H,7H-[1,3]oxazolo[5,4-d]pyrimidine-7-thione and 2-aryl-6H,7H-[1,3]thiazolo[5,4-d]pyrimidine-7-thione using 2-aroylaminomalonodiamide." Russian Journal of General Chemistry 83, no. 3 (March 2013): 572–76. http://dx.doi.org/10.1134/s1070363213030298.

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39

Abu-Hashem, Ameen Ali, Sami A. Al-Hussain, and Magdi E. A. Zaki. "Synthesis of Novel Benzodifuranyl; 1,3,5-Triazines; 1,3,5-Oxadiazepines; and Thiazolopyrimidines Derived from Visnaginone and Khellinone as Anti-Inflammatory and Analgesic Agents." Molecules 25, no. 1 (January 5, 2020): 220. http://dx.doi.org/10.3390/molecules25010220.

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Novel (4-methoxy or 4,8-dimethoxy)-3-methyl-N-(6-oxo-2-thioxo-1,2,3, 6-tetrahydro- pyrimidin-4-yl) benzo [1,2-b: 5, 4-b’] difuran-2-carboxamide (5a–b) has been synthesized by the reaction of visnagenone–ethylacetate (2a) or khellinone–ethylacetate (2b) with 6-aminothiouracil in dimethylformamide or refluxing of benzofuran-oxy-N-(2-thioxopyrimidine) acetamide (4a–b) in sodium ethoxide to give the same products (5a,b) in good yields. Thus, compounds 5a–b are used as an initiative to prepare many new heterocyclic compounds such as 2-(4-(3-methylbenzodifuran- 2-carbox-amido) pyrimidine) acetic acid (6a–b), N-(thiazolo[3, 2-a]pyrimidine)-3-methylbenzo- difuran-2-carboxamide (7a–b), N-(2-thioxopyrimidine)-methylbenzodifuran-2-carbimidoylchloride (8a–b), N-(2-(methyl-thio) pyrimidine)-3-methylbenzodifuran-2-carbimidoylchloride (9a–b), N-(2, 6 -di(piperazine or morpholine)pyrimidine)-1-(3-methylbenzodifuran)-1-(piperazine or morpholine) methanimine(10a–d), 8-(methylbenzodifuran)-thiazolopyrimido[1,6-a][1,3,5]triazine-3,5-dione (11a –b), 8-(3-methyl benzodifuran)-thiazolopyrimido[6,1-d][1,3,5]oxadiazepine-trione (12a–b), and 2,10 -di(sub-benzylidene)-8-(3-methylbenzodifuran)-thiazolopyrimido[6,1-d][1,3,5]oxadiazepine-3,5,11- trione (13a–f). All new chemical structures were illustrated on the basis of elemental and spectral analysis (IR, NMR, and MS). The new compounds were screened as cyclooxygenase-1/ cyclooxygenase-2 (COX-1/COX-2) inhibitors and had analgesic and anti-inflammatory activities. The compounds 10a–d and 13a–f had the highest inhibitory activity on COX-2 selectivity, with indices of 99–90, analgesic activity of 51–42% protection, and anti-inflammatory activity of 68%–59%. The inhibition of edema for the same compounds, 10a–d and 13a–f, was compared with sodium diclofenac as a standard drug.

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40

Seela, Frank, Simone Budow, and Xiaohua Peng. "7-Deazapurine (Pyrrolo[2,3-d]pyrimidine) 2-Deoxyribonucleosides: Syntheses and Transformations." Current Organic Chemistry 16, no. 2 (January 1, 2012): 161–223. http://dx.doi.org/10.2174/138527212798993086.

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41

Brændvang, Morten, and Lise-Lotte Gundersen. "4-(2-Furyl)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-d]pyrimidine." Acta Crystallographica Section E Structure Reports Online 63, no. 6 (May 10, 2007): o2849. http://dx.doi.org/10.1107/s1600536807021952.

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42

Briansó, J. L., J. F. Piniella, G. Germain, M. Garriga, and P. Victory. "4-Amino-2-bromo-6-methyl-5,6,7,8-tetrahydropyrido[2,3-d]-pyrimidine." Zeitschrift für Kristallographie 177, no. 3-4 (January 1986): 171–75. http://dx.doi.org/10.1524/zkri.1986.177.3-4.171.

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43

Salari, Maryam, Alireza Hassanabadi, and Mohammad H. Mosslemin. "Synthesis of Trans-6-(4-Chlorobenzoyl)-7-(Aryl)-1,3-Dimethyl-6,7-Dihydrofuro[3,2-d]Pyrimidine-2,4-Diones Using Choline Hydroxide as an Efficient Catalyst in an Aqueous Medium." Journal of Chemical Research 41, no. 3 (March 2017): 139–42. http://dx.doi.org/10.3184/174751917x14859570937794.

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A green and efficient synthesis of the trans-6-(4-chlorobenzoyl)-7-(aryl)-1,3-dimethyl-6,7-dihydrofuro[3,2-d]pyrimidine-2,4-diones has been achieved via a three-component, one-pot condensation of 2-[2-(4-chlorophenyl)-2-oxoethyl)]isoquinolinium bromide with 1,3-dimethylbarbituric acid and an aromatic aldehyde in the presence of catalytic amounts of choline hydroxide in water under reflux conditions. This gives trans-6-(4-chlorobenzoyl)-7-(aryl)-1,3-dimethyl-6,7-dihydrofuro[3,2-d]pyrimidine-2,4-diones in excellent yield and in short reaction times.

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44

Mahmoud, M. R., A. A. Shalaby, T. A. Gad, and A. A. El-Khamry. "A facile synthesis and heteroannulation of pyrido[2,3-d]pyrimidine and related heterocyclic systems." Journal of Chemical Research 2009, no. 10 (October 2009): 612–15. http://dx.doi.org/10.3184/030823409x12523324765777.

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7-Amino-1,2,3,4-tetrahydro-4-oxo-2-thioxo-5-(3,4,5-trimethoxyphenyl)pyrido[2,3- d]pyrimidine (1) was prepared and reacted with methyl iodide and ethyl chloroacetate to give the S-alkylated products 2 and 3, respectively. The reaction of 1 or 3 with hydrazine hydrate yielded the same 2-hydrazino derivative 4. Treatment of 4 with 2,4-pentanedione, 2-acetylcyclohexanone and ethyl acetoacetate afforded the corresponding pyrazolylpyrido[2,3- d]pyrimidine derivatives (5–7), while phthalic anhydride gave the phthalazinyl compound 8. Ethoxymethylenemalononitrile with the hydrazine 4 formed the fused 1,2,4-triazepine 9, while triazolopyrido[2,3- d]pyrimidines were obtained from the reaction of 4 with benzylidene malononitrile or benzaldehyde (forming 10), acetic acid/anhydride (giving 11), and ethyl chloroformate (giving 12).

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45

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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46

Liu, Mingxing, Jiarong Li, Hongxin Chai, Kai Zhang, Deli Yang, Qi Zhang, and Daxin Shi. "A convenient four-component one-pot strategy toward the synthesis of pyrazolo[3,4-d]pyrimidines." Beilstein Journal of Organic Chemistry 11 (November 6, 2015): 2125–31. http://dx.doi.org/10.3762/bjoc.11.229.

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An efficient one-pot synthesis of pyrazolo[3,4-d]pyrimidine derivatives by the four-component condensation of hydrazines, methylenemalononitriles, aldehydes and alcohols has been developed via two different reaction pathways. The structures of target products were characterized by IR spectroscopy, NMR (1H and 13C) spectroscopy and HRMS (ESI) spectrometry. The crystal structure of 4-ethoxy-6-(2-nitrophenyl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine was determined by single crystal X-ray diffraction.

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47

Abdelhamid, Abdou O., and Sobhi M. Gomha. "Synthesis of New Pyrazolo[1,5-a]pyrimidine, Triazolo[4,3-a]pyrimidine Derivatives, and Thieno[2,3-b]pyridine Derivatives from Sodium 3-(5-Methyl-1-phenyl-1H-pyrazol-4-yl)-3-oxoprop-1-en-1-olate." Journal of Chemistry 2013 (2013): 1–7. http://dx.doi.org/10.1155/2013/327095.

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Abstract:

Condensation of sodium 3-oxo-3-(1-phenyl-1H-pyrazol-4-yl)prop-1-en-1-olate (2) with several heterocyclic amines, cyanoacetamide, cyanothioacetamide, and 2-cyanoacetohydrazide gives pyrazolo[1,5-a]pyrimidines (5a–d), pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine (9), benzo[4,5]imidazo[1,2-a]pyrimidine (10), [1,2,4]triazolo[1,5-a]pyrimidine (11), and pyridine derivatives (12–14). Also, thieno[2,3-b]pyridines (15–18) were synthesized via pyridinethione (13) withα-halo ketones andα-halo ester. Structures of the newly synthesized compounds were elucidated by elemental analysis, spectral data, alternative synthetic routes, and chemical transformation whenever possible.

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48

Holman, Michelle A., Natalie M. Williamson, and A. David Ward. "Preparation and Cyclization of Some N-(2,2-Dimethylpropargyl) Homo- and Heteroaromatic Amines and the Synthesis of Some Pyrido[2,3-d]pyrimidines." Australian Journal of Chemistry 58, no. 5 (2005): 368. http://dx.doi.org/10.1071/ch04260.

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Abstract:

The Cu(i) catalyzed cyclization of o-substituted N-(2,2-dimethylpropargyl)anilines yields 8-substituted 2,2-dimethyl-1,2-dihydroquinolines, while m-substituted analogues provide a mixture of 5- and 7-substituted dihydroquinoline systems. This reaction can be extended to 2-amino-N-(2,2-dimethylpropargyl)anthracene, yielding a dihydronaphtho[2,3-f]quinoline product, and to aminoquinoline derivatives, which yield substituted phenanthroline products. Pyridine analogues did not cyclize, apparently because of complexation with the copper reagent. An alternative synthetic approach to these cyclized products, when complexation may be a problem, is illustrated by the following example. 2-Chloro-4-N-(2,2-dimethylpropargyl)pyrimidine was reduced using a Lindlar catalyst to the corresponding alkene which did not undergo an amino-Claisen rearrangement. However, the 5-bromopyrimidine alkene analogue underwent addition with phenylselanyl bromide to give a product that cyclized, using butyllithium, to a pyrido[2,3-d]pyrimidine selenium-containing product from which the selenium moiety could be removed to yield either a dihydro- or a tetrahydro-pyrido[2,3-d]pyrimidine system. A Heck reaction on the 5-bromopyrimidine alkene gave a 5-methylene-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine.

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49

Harnden, MR, and DT Hurst. "The Chemistry of Pyrimidinethiols. III. The Synthesis of Some Substituted Pyrimidinthiols and Some Thiazolo[5,4-D]pyrimidines." Australian Journal of Chemistry 43, no. 1 (1990): 55. http://dx.doi.org/10.1071/ch9900055.

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Abstract:

The preparation of a number of pyrimidinethiols and (substituted) thiopyrimidines has been carried out. The reaction of 5-acetylamino-2-aminopyrimidine-4,6-diol with phosphorus penta -sulfide in pyridine gave 5-amino-2-methylthiazolo[5,4-d]pyrimidine-7-thiol which was used to prepare several additional novel pyrimidine derivatives. Hydrolysis of the 4-carboxymethylthio derivative by using 5M hydrochloric acid gave 2,5-diamino-6-mercaptopyrimidin-4-ol hy -drochloride whilst hydrolysis of 2-methyl-7-methylthiothiazolo[5,4-d]pyrimidin-5-amine gave the corresponding 4-hydroxy derivative. Several 4-arenecarbonylmethylthio derivatives were recovered unchanged from such hydrolysis reactions.

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50

Yamamoto, Seigi, Soyoung Park, and Hiroshi Sugiyama. "Development of a visible nanothermometer with a highly emissive 2′-O-methylated guanosine analogue." RSC Advances 5, no. 126 (2015): 104601–5. http://dx.doi.org/10.1039/c5ra24756j.

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