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Journal articles on the topic 'Dihydropyrrolone'

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Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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1

Melekhina, Valeriya G., Andrey N. Komogortsev, Boris V. Lichitsky, Vitaly S. Mityanov, Artem N. Fakhrutdinov, Arkady A. Dudinov, Vasily A. Migulin, Yulia V. Nelyubina, Elizaveta K. Melnikova, and Michail M. Krayushkin. "One-pot synthesis of substituted pyrrolo[3,4-b]pyridine-4,5-diones based on the reaction of N-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-arylethyl)acetamide with amines." Beilstein Journal of Organic Chemistry 15 (November 25, 2019): 2840–46. http://dx.doi.org/10.3762/bjoc.15.277.

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The condensation of primary amines with N-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-arylethyl)acetamides was explored. Thus, a previously unknown recyclization of the starting material was observed in acidic ethanol in the presence of an amine, which provided the corresponding dihydropyrrolone derivative as the major reaction product. Based on this transformation, a practical and convenient one-pot synthetic method for substituted pyrrolo[3,4-b]pyridin-5-ones could be devised.

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2

Ho, Kitty Ka Kit, Nerida Cole, Renxun Chen, Mark D. P. Willcox, Scott A. Rice, and Naresh Kumar. "Immobilization of Antibacterial Dihydropyrrol-2-ones on Functional Polymer Supports To Prevent Bacterial InfectionsIn Vivo." Antimicrobial Agents and Chemotherapy 56, no. 2 (December 5, 2011): 1138–41. http://dx.doi.org/10.1128/aac.05814-11.

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ABSTRACTAntibiotic-resistantStaphylococcus aureusis of great concern, as it causes a wide range of life-threatening infections. The current study demonstrates that dihydropyrrolone (DHP)-coated polyacrylamide substrates are effective in reducing the number of culturable clinical isolates ofS. aureusin vitroin a dose-dependent manner and are able to reduce the pathogenic potential of staphylococcal infection in a subcutaneous infection model. Covalently bound DHPs therefore show great potential for use as an antimicrobial strategy in device-related applications.

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3

Tian, Shuanbao, and Yongbing Hao. "Sulfuric Acid-Modified Polyethylene Glycol 6000 Catalyzed Synthesis of Dihydropyrrolone." Chinese Journal of Organic Chemistry 33, no. 10 (2013): 2232. http://dx.doi.org/10.6023/cjoc201304040.

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4

Pandya, Keyur, Bhavesh Dave, Rajesh Patel, and Piyush Desai. "In Silico Approach Towards the Prediction of Drug-likeness, in Vitro Microbial Investigation and Formation of Dihydropyrrolone Conjugates." Advanced Journal of Chemistry-Section A 3, no. 4 (June 1, 2020): 378–90. http://dx.doi.org/10.33945/sami/ajca.2020.4.1.

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5

Biletzki, Tobias, Thomas Elschner, Toni Neuwirth, Helmar Görls, and Wolfgang Imhof. "Synthesis and structural characterization of imines from 2,3-diphenylbutane-1,4-diamine and their ruthenium catalyzed transformation to bis-(1,3-dihydropyrrolone) derivatives." Arkivoc 2012, no. 3 (July 15, 2012): 457–69. http://dx.doi.org/10.3998/ark.5550190.0013.331.

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6

Singh, Mandavi, Shyam Babu Singh, Shahin Fatma, Preyas Ankit, and Jagdamba Singh. "Development of five membered heterocyclic frameworks via [3+2] cycloaddition reaction in an aqueous micellar system." New J. Chem. 38, no. 7 (2014): 2756–59. http://dx.doi.org/10.1039/c4nj00325j.

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A series of novel dihydropyrrolo[2,1-a]isoquinolines and dihydropyrrolo[1,2-a]quinolines have been synthesized from isoquinolines/quinolines, various substituted phenacyl bromides and substituted dialkylacetylenedicarboxylates via [3+2] cycloaddition reaction.

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7

Kreher, Richard P., and Gerald Dyker. "Struktur und Reaktivität von isoanellierten heterocyclischen Systemen mit Anπ- und (4n+2)π-Elektronen, XII [1]. 2-tert-Butyl-4-methyl-2,4-dihydropyrrolo[3,4-b]indole: Tricyclische Hetarene mit isoanellierten Pyrrolringen / Structure and Reactivity of Isoannelated Heterocyclic Systems with 4nπ- and (4n+2)π-Electrons, XII [1] 2-terr-Butyl-4-methyl-2,4-dihydropyrrolo[3,4-b]indoles: Tricyclic Hetarenes with Isoannelated Pyrrole Rings." Zeitschrift für Naturforschung B 42, no. 4 (April 1, 1987): 473–77. http://dx.doi.org/10.1515/znb-1987-0414.

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2-tert-Butyl-4-methyl-2,4-dihydropyrrolo[3,4-b]indole (4a) has been prepared via selective reduction of 2-rm-butyl-4-methyl-2,4-dihydropyrrolo[3,4-b]indol-l(2H)-one or -3(2H)-one 5 and 6 with diisobutylaluminiumhydride. The same precursors 5 and 6 can be transformed into 2-tert-butyl-4-methyl-2,4-dihydropyrrolo[3,4-b]indoles (4b) and (4c) bearing a methoxy group in 1- or 3-position via a two step procedure consisting in O-alkylation and CH-deprotonation. NMR Investigations afford an insight into the structure of the stable tricyclic hetarenes.

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8

Guo, Yong En, Xiao Guang Niu, Cai Ju Zhou, Jie Chu, Wei Wei Xu, and Guo Zhen Fang. "Design and Preparation of 1H-3, 4-Dihydropyrrolo[1,2-a] Pyrazin-1-One via 1H-3,4-Dihydropyrrolo[1,2-C] [1,4] Oxazin-1-One Route." Advanced Materials Research 343-344 (September 2011): 1242–47. http://dx.doi.org/10.4028/www.scientific.net/amr.343-344.1242.

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With 2-pyrrolyltrichloroacetone as major starting material, unreported 1H-3,4-dihydropyrrolo- [1,2-a]pyrazin-1-one was prepared successively by its monoesterification with ethylene glycol, bromine displacement of hydroxy group, cyclization to lactone and its amidation. Unreported 7-aroyl-1H-3,4-dihydropyrrolo[1,2-c][1,4]oxazin-1-one compounds were also synthesized in turn by 2-pyrrolyl-trichloroacetone’s Friedel-Crafts acylation and cyclization. Their structures were characterized by IR, 1H NMR, 13C NMR, MS, HRMS, etc.

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9

Liao, Shao Han, Dai Hua Hu, Ai Ling Wang, and De Peng Li. "Novel 5,6-Dihydropyrrolo[2,1-a]isoquinolines as Scaffolds for Synthesis of Lamellarin Analogues." Evidence-Based Complementary and Alternative Medicine 2011 (2011): 1–6. http://dx.doi.org/10.1155/2011/103425.

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As core skeletons of lamellarins: 5,6-Dihydropyrrolo[2,1-a]isoquinolines are one of the important alkaloids that exhibit significant biological activities, in this study, an efficient synthetic route was described for two novel compounds, 5,6-dihydropyrrolo[2,1-a]isoquinolinesIandII. CompoundIwas synthesized from isovanillin with 28.3% overall yield by a six-step reaction whileIIfrom 2-(3,4-dimethoxyphenyl) ethanamine was with 61.6% overall yield by a three-step reaction. And the structures of these two compounds were confirmed by means of IR spectrum,1H NMR,13C NMR, MS, HRMS, and melting point measurements.

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10

Belguedj, Roumaissa, Sofiane Bouacida, Hocine Merazig, Ali Belfaitah, Aissa Chibani, and Abdelmalek Bouraiou. "Synthesis and crystal structures of three novel benzimidazole/benzoindolizine hybrids." Zeitschrift für Naturforschung B 71, no. 3 (March 1, 2016): 231–39. http://dx.doi.org/10.1515/znb-2015-0164.

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AbstractThree benzoindolizine derivatives, 1, 2, and 3, were obtained via 1,3-dipolar cycloaddition. The reaction of 1-(2′-benzimidazolylmethyl)isoquinolinium ylides with dimethyl acetylenedicarboxylate gave a mixture of pyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate (1) and 1,10b-dihydropyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate (2) derivatives containing a benzimidazole moiety. The reaction of this isoquinolinium N-ylide with dimethyl maleate gave an unexpected 2,3-dihydropyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate (3). The structures of all reported compounds have been examined by X-ray crystallography, mass spectrometry, and NMR spectroscopy.

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11

Wang, Wenhui, Jinwei Sun, Huayou Hu, and Yun Liu. "Copper-catalyzed aerobic cyclizations of tetrahydroisoquinolines with bromoketones and alkenes for the synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines." Organic & Biomolecular Chemistry 16, no. 10 (2018): 1651–58. http://dx.doi.org/10.1039/c7ob03048g.

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12

Huang, Zhusheng, Zonghao Dai, Jin Zhu, Fulai Yang, and Qingfa Zhou. "Synthesis of functionalized 2,5-dihydropyrrole derivatives via a convenient [3 + 2] annulation of azomethine ylides with allenoates." Organic & Biomolecular Chemistry 16, no. 36 (2018): 6638–46. http://dx.doi.org/10.1039/c8ob01946k.

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13

Zabaleta, Nagore, Uxue Uria, Efraim Reyes, Luisa Carrillo, and Jose L. Vicario. "Ion-pairing catalysis in the enantioselective addition of hydrazones to N-acyldihydropyrrole derivatives." Chemical Communications 54, no. 64 (2018): 8905–8. http://dx.doi.org/10.1039/c8cc05311a.

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14

Sun, Zhen, Zheng Li, and Wei-Wei Liao. "An organocatalytic hydroalkoxylation/Claisen rearrangement/Michael addition tandem sequence: divergent synthesis of multi-substituted 2,3-dihydrofurans and 2,3-dihydropyrroles from cyanohydrins." Green Chemistry 21, no. 7 (2019): 1614–18. http://dx.doi.org/10.1039/c8gc03978j.

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15

Banfield, JE, GD Fallon, and BM Gatehouse. "Heterocyclic-Derivatives of Guanidine. VI. Formation and X-Ray Structure Determination of 2-Dimethylamino-7,8-diphenyl-4,6-dihydropyrrolo[1,2-a]pyrimidine-4,6-dione." Australian Journal of Chemistry 40, no. 5 (1987): 1003. http://dx.doi.org/10.1071/ch9871003.

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The structure N-(2-dimethylamino-4-oxo-7,8-diphenyl-4,6-dihydropyrrolo [l,2-a]pyrimidi n-6-yl-idene)acetamide (3) is proposed for a compound derived from the action of ketene on 2-(2-imino- 3,4-diphenyl-2H-pyrrol-5-yl)-1,1,3-trimethylguanidine (1; R1 = R2 = R3 = Me) on the basis of the crystal structure of its hydrolysis product, the oxo-compound 2-dimethylamino-7,8-diphenyl-4,6-dihydropyrrolo[l,2-a]pyrimidine-4,6-dione (4), the structure of which was determined by X-ray analysis. A lower homologue of (3), N-(2-methylamino-4-oxo-7,8-diphenyl-4,6-dihydro- pyrrolo[l,2-a]pyrimidin-6-ylidene)acetamide (2), and some related compounds are described.

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16

Cui, Hai-Lei. "FeCl2 catalyzed direct modification of dihydropyrrolo[2,1-a]isoquinolines with phenols." Organic & Biomolecular Chemistry 18, no. 21 (2020): 4085–89. http://dx.doi.org/10.1039/d0ob00917b.

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17

He, Yinghui, Chang Guo, Bin Sun, Jesse Quinn, and Yuning Li. "(3E,7E)-3,7-Bis(2-oxoindolin-3-ylidene)-5,7-dihydropyrrolo[2,3-f]indole-2,6(1H,3H)-dione based polymers for ambipolar organic thin film transistors." Chemical Communications 51, no. 38 (2015): 8093–96. http://dx.doi.org/10.1039/c5cc01021g.

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18

Almohaywi, Basmah, Tsz Tin Yu, George Iskander, Daniel S. H. Chan, Kitty K. K. Ho, Scott Rice, David StC Black, Renate Griffith, and Naresh Kumar. "Dihydropyrrolones as bacterial quorum sensing inhibitors." Bioorganic & Medicinal Chemistry Letters 29, no. 9 (May 2019): 1054–59. http://dx.doi.org/10.1016/j.bmcl.2019.03.004.

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19

Jiang, Xue-Fei, Hao Tan, and Hai-Lei Cui. "FeCl3 mediated dimerization of dihydropyrrolo[2,1-a]isoquinolines and chlorination of tetrasubstituted pyrroles." Organic & Biomolecular Chemistry 18, no. 4 (2020): 660–65. http://dx.doi.org/10.1039/c9ob02607j.

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We have developed a mild FeCl₃-mediated dimerization of dihydropyrrolo[2,1-a]isoquinolines through oxidative homocoupling (35–>99% yield) and chlorination of tetrasubstituted pyrroles (18–70% yield).

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20

Lee, Jeong Hwa, Seok Hyun Yoon, Seonghyeon Nam, and Ikyon Kim. "One-pot three-component coupling access to 1,2-dihydropyrrolo[1,2-a]pyrazine-1-phosphonates: multi-functionalization of a pyrazine unit." Organic & Biomolecular Chemistry 19, no. 27 (2021): 6066–84. http://dx.doi.org/10.1039/d1ob00885d.

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A highly efficient domino one-pot three-component Kabachnik–Fields coupling-intramolecular dehydrative cyclization process allowed facile access to 1,2-dihydropyrrolo[1,2-a]pyrazine-1-phosphonates with a densely-functionalized pyrazine unit.

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21

Purba, Prioti Choudhury, Soumalya Bhattacharyya, Manoranjan Maity, Sujay Mukhopadhyay, Prodip Howlader, and Partha Sarathi Mukherjee. "Linkage induced enhancement of fluorescence in metal–carbene bond directed metallacycles and metallacages." Chemical Communications 55, no. 57 (2019): 8309–12. http://dx.doi.org/10.1039/c9cc04444b.

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Four new metal–carbene based metallacycles and metallocages have been obtained using non-AIE active 1,4-dihydropyrrolo[3,2-b]pyrrole based imidazolium ligands. These final assemblies show linkage induced enhanced emission via rigidification.

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22

Elghamry, Ibrahim, and Dietrich Dopp. "A New Asymmetric Photoisomerization of 2,3-Dihydropyrrolo[1,2-b]benzisothiazole 5,5-Dioxides." Journal of the Korean Chemical Society 54, no. 6 (December 20, 2010): 727–30. http://dx.doi.org/10.5012/jkcs.2010.54.6.727.

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23

Choi, Eun Joung, and Seung Bum Park. "Unique photophysical properties of 9-styryl-1,2-dihydropyrrolo[3,4-β]indolizin-3-one and its efficient synthesis via direct C–H activation." Organic & Biomolecular Chemistry 13, no. 18 (2015): 5202–8. http://dx.doi.org/10.1039/c5ob00551e.

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A styryl Seoul-Fluor (SF) skeleton was rationally designed by introducing an olefin unit at the C-9 of 1,2-dihydropyrrolo[3,4-β]indolizin-3-one via regioselective direct C–H activation, affording average 39 nm of bathochromic shift.

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24

Matveeva, Maria, Tatiana Borisova, Alexander Titov, Lada Anikina, Svetlana Dyachenko, Grigorii Astakhov, Alexey Varlamov, and Leonid Voskressensky. "Domino Reactions of 1-Aroyl-3,4-dihydroisoquinolines with α,β-Unsaturated Aldehydes." Synthesis 49, no. 23 (August 22, 2017): 5251–57. http://dx.doi.org/10.1055/s-0036-1588486.

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An efficient synthesis of pyrrolo[2,1-a]isoquinolines by a domino reaction from a variety of 3,4-dihydropyrrolo[2,1-a]isoquinolines and α,β-unsaturated aldehydes in the absence of catalyst in good yields under microwave irradiation, is reported.

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25

Jiang, Bo, and Min Shi. "Rhodium(ii)-catalyzed intermolecular [3 + 2] annulation of N-vinyl indoles with N-tosyl-1,2,3-triazoles via an aza-vinyl Rh carbene." Organic Chemistry Frontiers 4, no. 12 (2017): 2459–64. http://dx.doi.org/10.1039/c7qo00703e.

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This study opens up a new synthetic approach for the construction of various functionalized indoles having a dihydropyrrole moiety from the Rh(ii)-catalyzed annulation of N-vinyl indoles with 4-aryl-N-tosyl-1,2,3-triazoles under mild conditions.

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26

Pinna, Gérard Aimè, Mario Sechi, Giuseppe Paglietti, and Maria Antonietta Pirisi. "Addition reactions of Acetylenic Esters to 6,7-Dihydrobenzo[B]Furan-4(5H)-One, 6,7-Dihydroindol-4(5H)-One, 5,6-Dihydrobenzo[B]Furan-7(6H)-One and 5,6-Dihydroindol-7(6H)-One Ketoximes. Formation of Reduced Furo[G]- and Pyrrolo[G]-Indoles." Journal of Chemical Research 2003, no. 3 (March 2003): 117–20. http://dx.doi.org/10.3184/030823403103173426.

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Thermal rearrangement of 6,7-dihydrobenzo[ b]furan-4(5 H)-one and 4,5,6,7-tetrahydroindol-4-one 4(7)- O-( E)-(1,2-dimethoxycarbonylvinyl)ketoximes gave 4,5-dihydrofuro[2,3 g]- and 4,5-dihydropyrrolo[2,3 g]- and [3,2- g] indoles, three novel tricyclic systems

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27

Dhar, Abhishek, Nadavala Siva Kumar, Mohammad Asif, and Rohit L. Vekariya. "Fabrication of D–π–A sensitizers based on different donors substituted with a dihydropyrrolo[3,4-c]pyrrole-1,4-dione bridge for DSSCs: influence of the CDCA co-absorbent." New Journal of Chemistry 42, no. 14 (2018): 12024–31. http://dx.doi.org/10.1039/c8nj00847g.

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The effect of co-absorbance on the performance of DSSC devices with a new design of dimer sensitizers possessing a 2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (DPP) bridge and various donor groups (carbazole, diphenyl amine, indole) are reported in the present work.

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28

Noda, Kyoko, Naoko Terasawa, and Masatsune Murata. "Formation scheme and antioxidant activity of a novel Maillard pigment, pyrrolothiazolate, formed from cysteine and glucose." Food & Function 7, no. 6 (2016): 2551–56. http://dx.doi.org/10.1039/c5fo01625h.

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We recently identified 6-hydroxy-3[R],7a[S]-dimethyl-7-oxo-2,3-dihydropyrrolo[2,1-b]thiazole-3-calboxylic acid, a novel pyrrolothiazole derivative carrying a carboxy group and named pyrrolothiazolate, as a Mallard pigment formed from l-cysteine and d-glucose.

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29

Xing, Siyang, Junsuo Guo, Yuhan Wang, Chenyu Wang, Kui Wang, and Bolin Zhu. "General and efficient synthesis of 1,2-dihydropyrrolo[3,4-b]indol-3-ones via a formal [3 + 2] cycloaddition initiated by C–H activation." Organic Chemistry Frontiers 7, no. 24 (2020): 4057–63. http://dx.doi.org/10.1039/d0qo00922a.

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A [Cp*RhCl₂]₂-catalyzed formal [3 + 2] cycloaddition involving a sequential coupling reaction initiated by C–H activation and aza-Michael addition has been developed for the general and efficient synthesis of 1,2-dihydropyrrolo[3,4-b]indol-3-ones.

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30

Liao, Hui, and Qiuhua Zhu. "Water–DMSO-promoted one-pot synthesis of two new series of dihydropyrrolo[2,3-h]quinolines." Organic & Biomolecular Chemistry 18, no. 2 (2020): 215–19. http://dx.doi.org/10.1039/c9ob02342a.

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Two new series of dihydropyrrolo[2,3-h]quinolines 4 and 6 were synthesized via a three-component reaction synergistically activated by water and DMSO, and new pyrrolo[2,3-h]quinolines 10 can be obtained by oxidation of 4 using Cu(NO₃)₂ as oxidant.

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31

Miksch, April M., Annalena Riffelt, Ricardo Oliveira, Johannes Kästner, and Germán Molpeceres. "Hydrogenation of small aromatic heterocycles at low temperatures." Monthly Notices of the Royal Astronomical Society 505, no. 3 (May 27, 2021): 3157–64. http://dx.doi.org/10.1093/mnras/stab1514.

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ABSTRACT The recent wave of detections of interstellar aromatic molecules has sparked interest in the chemical behaviour of aromatic molecules under astrophysical conditions. In most cases, these detections have been made through chemically related molecules, called proxies, that implicitly indicate the presence of a parent molecule. In this study, we present the results of the theoretical evaluation of the hydrogenation reactions of different aromatic molecules (benzene, pyridine, pyrrole, furan, thiophene, silabenzene, and phosphorine). The viability of these reactions allows us to evaluate the resilience of these molecules to the most important reducing agent in the interstellar medium, the hydrogen atom (H). All significant reactions are exothermic and most of them present activation barriers, which are, in several cases, overcome by quantum tunnelling. Instanton reaction rate constants are provided between 50 and 500 K. For the most efficiently formed radicals, a second hydrogenation step has been studied. We propose that hydrogenated derivatives of furan and pyrrole, especially 2,3-dihydropyrrole, 2,5-dihydropyrrole, 2,3-dihydrofuran, and 2,5-dihydrofuran, are promising candidates for future interstellar detections.

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32

Taskaya, Sultan, Nurettin Menges, and Metin Balci. "Gold-catalyzed formation of pyrrolo- and indolo-oxazin-1-one derivatives: The key structure of some marine natural products." Beilstein Journal of Organic Chemistry 11 (May 28, 2015): 897–905. http://dx.doi.org/10.3762/bjoc.11.101.

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Various N-propargylpyrrole and indolecarboxylic acids were efficiently converted into 3,4-dihydropyrrolo- and indolo-oxazin-1-one derivatives by a gold(III)-catalyzed cyclization reaction. Some of the products underwent TFA-catalyzed double bond isomerization and some did not. Cyclization reactions in the presence of alcohol catalyzed by Au(I) resulted in the formation of hemiacetals after cascade reactions.

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33

He, Yan, Fang Wang, Xinying Zhang, and Xuesen Fan. "C(sp3)–H dehydrogenation and C(sp2)–H alkoxy carbonylation of inactivated cyclic amines towards functionalized N-heterocycles." Chemical Communications 53, no. 28 (2017): 4002–5. http://dx.doi.org/10.1039/c6cc10227a.

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A novel and efficient synthesis of tetrahydropyridine-, dihydropyrrole-, and tetrahydroazepine-3-carboxylates via cascade reactions of cyclic amines with CO and alcohols is presented. To our knowledge, this should be the first example in which functionalized N-heterocycles were prepared through Pd-catalyzed C(sp³)–H dehydrogenation and C(sp²)–H carbonylation of cyclic amines.

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34

Yena, Maryna, and Nataliya Dzyubenko. "EFFECT OF PYRROLE DERIVATIVE ON THE RAT COLONIC MUCOSA COMPARED TO 5-FLUOROURACIL." EUREKA: Life Sciences 5 (September 30, 2016): 18–24. http://dx.doi.org/10.21303/2504-5695.2016.00152.

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Prevention the development of malignant tumors and treatment of cancer patients remains an important problem today. In spite of substantive progress in the cancer diagnostics and treatment cancer occupies one of the main places in human morbidity and mortality in the World. Targeted therapy is an alternative to traditional one through targeted action on tumor cells and relatively low toxicity. Inhibitor of membrane tyrosine kinases dihydropyrrole derivative 5-amino-4-(1,3-benzothiazole-2-yl)-1-(3- methoxyphenyl)-1,2-dihydro-3Н-pyrrol-3-one (D-1) has significant antitumor activity on colorectal cancer and low toxicity acting in effective dose. However, to assess the D-1 therapeutic gap the investigation of its higher doses is necessary. The investigation was aimed at D-1 effects applied at different doses compared to 5-fluorouracil one on rats ascending colon mucosa. The research has found out that the dihydropyrrole derivative has no damaging effect on the colon of rats, whereas the administration of 5-fluorouracil causes marked mucosal lesion of the ascending colon. Hereby D-1 low toxicity to ascending colon mucosa compared to 5-FU and wide therapeutic gap of the first was concluded.

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35

Tang, Xiang-Ying, Yue-fa Gong, and Heng-rui Huo. "Metal-Free Synthesis of Pyrrolo[1,2-a]quinoxalines Mediated by TEMPO Oxoammonium Salts." Synthesis 50, no. 14 (June 13, 2018): 2727–40. http://dx.doi.org/10.1055/s-0037-1610131.

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We herein describe a novel TEMPO oxoammonium salt initiated Pictet–Spengler reaction of imines, generated in situ from carbonyl compounds and pyrrole- or indole-containing substrates, to afford 4,5-dihydropyrrolo[1,2-a]quinoxalines or 5,6-dihydroindolo[1,2-a]quinoxalines in good to excellent yields. Moreover, a one-pot synthesis of a biologically important quinoxaline is achieved via a cyclization–dehydrogenation process using one equivalent of the oxoammonium salt.

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36

Nord, Christina, Jolanta J. Levenfors, Joakim Bjerketorp, Christer Sahlberg, Bengt Guss, Bo Öberg, and Anders Broberg. "Antibacterial Isoquinoline Alkaloids from the Fungus Penicillium Spathulatum Em19." Molecules 24, no. 24 (December 17, 2019): 4616. http://dx.doi.org/10.3390/molecules24244616.

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In the search for new microbial antibacterial secondary metabolites, two new compounds (1 and 2) were isolated from culture broths of Penicillium spathulatum Em19. Structure determination by nuclear magnetic resonance and mass spectrometry identified the compounds as 6,7-dihydroxy-5,10-dihydropyrrolo[1,2-b]isoquinoline-3-carboxylic acid (1, spathullin A) and 5,10-dihydropyrrolo[1,2-b]isoquinoline-6,7-diol (2, spathullin B). The two compounds displayed activity against both Gram-negative and -positive bacteria, including Escherichia coli, Acinetobacter baumannii, Enterobacter cloacae, Klebsiella pneumonia, Pseudomonas aeruginosa, and Staphylococcus aureus. Compound 2 was more potent than 1 against all tested pathogens, with minimal inhibitory concentrations down to 1 µg/mL (5 µM) against S. aureus, but 2 was also more cytotoxic than 1 (50% inhibitory concentrations 112 and 11 µM for compounds 1 and 2, respectively, towards Huh7 cells). Based on stable isotope labelling experiments and a literature comparison, the biosynthesis of 1 was suggested to proceed from cysteine, tyrosine and methionine via a non-ribosomal peptides synthase like enzyme complex, whereas compound 2 was formed spontaneously from 1 by decarboxylation. Compound 1 was also easily oxidized to the 1,2-benzoquinone 3. Due to the instability of compound 1 and the toxicity of 2, the compounds are of low interest as possible future antibacterial drugs.

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37

Shaik, Baji, Mujeeb Khan, Mohammed Rafi Shaik, Mohammed A. F. Sharaf, Doumbia Sekou, and Sang-Gyeong Lee. "A-π-D-π-A-Based Small Molecules for OTFTs Containing Diketopyrrolopyrrole as Acceptor Units." Micromachines 12, no. 7 (July 13, 2021): 817. http://dx.doi.org/10.3390/mi12070817.

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A-π-D-π-A-based small molecules 6,6′-((thiophene-2,5-diylbis(ethyne-2,1-diyl))bis(thiophene-5,2-diyl))bis(2,5-bis(2-ethylhexyl)-3-(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione) (TDPP-T) and 6,6′-(((2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-diyl)bis(ethyne-2,1-diyl))bis(thiophene-5,2-diyl))bis(2,5-bis(2-ethylhexyl)-3-(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione) (TDPP-EDOT) have been designed and synthesized. The diketopyrrolopyrrole acts as an electron acceptor, while the thiophene or 3,4-ethylenedioxythiophene acts as an electron donor. The donor–acceptor groups are connected by an ethynyl bridge to further enhance the conjugation. The optoelectronics, electrochemical, and thermal properties have been investigated. Organic thin film transistor (OTFT) devices prepared from TDPP-T and TDPP-EDOT have shown p-type mobility. In as cast films, TDPP-T and TDPP-EDOT have shown a hole mobility of 5.44 × 10−6 cm2 V−1 s−1 and 4.13 × 10−6 cm2 V−1 s−1, respectively. The increase in the mobility of TDPP-T and TDPP-EDOT OTFT devices was observed after annealing at 150 °C, after which the mobilities were 3.11 × 10−4 cm2 V−1 s−1 and 2.63 × 10−4 cm2 V−1 s−1, respectively.

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38

Nielsen, Christian B., and Thomas Bjørnholm. "New Regiosymmetrical Dioxopyrrolo- and Dihydropyrrolo-Functionalized Polythiophenes." Organic Letters 6, no. 19 (September 2004): 3381–84. http://dx.doi.org/10.1021/ol048659n.

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39

Terenin, V. I., E. V. Kabanova, N. A. Tselishcheva, M. A. Kovalkina, A. P. Pleshkova, and N. V. Zyk. "Acylation of 3,4-Dihydropyrrolo[1,2-a]pyrazines." Chemistry of Heterocyclic Compounds 40, no. 3 (March 2004): 351–60. http://dx.doi.org/10.1023/b:cohc.0000028632.61226.cd.

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40

Prager, RH, and C. Tsopelas. "Approaches to the Synthesis of 5-Benzylidene-2-imidazolin-4-ones." Australian Journal of Chemistry 43, no. 2 (1990): 367. http://dx.doi.org/10.1071/ch9900367.

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Aromatic aldehydes , but not ketones, can be condensed with glycocyamidine . The corresponding alkylbenzylideneglycocyamidines may be made from glycidic esters by reaction with guanidine, followed by cyclization with acetic anhydride. A number of mono- and di -acetylated derivatives of 6,7-dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)- dione have been prepared, but failed to undergo the Darzens reaction. Bromo- and iodo-2-arylazoimidazoles, protected on nitrogen by the methoxyethoxymethyl group, failed to undergo clean lithiation.

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41

Katritzky, Alan R., Hai-Ying He, and Rong Jiang. "Convenient syntheses of dihydropyrrolo[2′,1′:3,4]pyrazino- and dihydropyrrolo[2′,1′:3,4][1,4]diazepino-[2,1-a]isoindolones." Tetrahedron Letters 43, no. 15 (April 2002): 2831–33. http://dx.doi.org/10.1016/s0040-4039(02)00350-7.

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42

Dyker, Gerald, and Richard P. Kreher. "Struktur und Reaktivität von isoanellierten heterocyclischen Systemen mit 4nπ- und (4n+2)π-Elektronen, XVII [1] Diels-Aider- und Michael-Additionsreaktionen von 3-Alkoxy-2,4-dihydropyrrolo[3,4-b]indolen mit Ethindicarbonsäuredialkylestern / Structure and Reactivity of Isoannelated Heterocyclic Systems with 4nπ- and (4n+2)π-Electrons, XVII [1] Diels-Alder and Michael Addition Reactions of 3-Alkoxy-2,4-dihydropyrrolo[3,4-b]indoles with Dialkyl Acetylenedicarboxylates." Zeitschrift für Naturforschung B 43, no. 12 (December 1, 1988): 1656–61. http://dx.doi.org/10.1515/znb-1988-1221.

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Abstract The reactions of 2-rm-butyl-3-methoxy-4-methyl-2,4-dihydropyrrolo[3,4-b]indole (3) with dialkyl acetylenedicarboxylates are decisively influenced by the solvent. In the presence of alcohols as protic and polar solvents Michael addition is prefered, while in aprotic and less polar solvents like ether the Diels-Alder reaction is favoured. Based on stereospecific hydrolysis and isotopic labeling dipolar intermediates are discussed. The results are of current interest for mechanistic and theoretical reasons

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43

Lyons, Thérèse, Cormac GM Gahan, and Timothy P. O'Sullivan. "Structure–activity relationships of furanones, dihydropyrrolones and thiophenones as potential quorum sensing inhibitors." Future Medicinal Chemistry 12, no. 21 (November 2020): 1925–43. http://dx.doi.org/10.4155/fmc-2020-0244.

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Since their initial isolation from the marine alga Delisea pulchra, bromofuranones have been investigated as potential inhibitors of quorum sensing (QS) in various bacterial strains. QS is an important mechanism by which bacteria co-ordinate their molecular response to the environment. QS is intrinsically linked to bacterial antibiotic resistance. Inspired by nature, chemists have developed a wide variety of synthetic analogs in an effort to elucidate the structure–activity relationships of these compounds, and to ultimately develop novel antimicrobial agents. In this work, we describe advances in this field while paying particular attention to apparent structure–activity relationships. This review is organized according to the main ring systems under investigation, namely furanones, dihydropyrrolones and thiophenones.

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44

Zlatoidský, Pavol, Elisa Martinelli, Emil Svensson, and Alexis Pruvost. "A Facile Access to Novel (5+5) Annellated Heterocycles: Synthesis of a Furopyrrole, an Imidazoimidazole and a Pyrroloimidazole." Synthesis 51, no. 18 (June 25, 2019): 3491–98. http://dx.doi.org/10.1055/s-0039-1689916.

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We describe the synthesis of an ethyl 3-aryl-6H-furo[2,3-b]pyrrole-5-carboxylate 2, a 5-aryl-1H-imidazo[1,2-a]imidazole 3, and an ethyl-1-aryl-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate 4 as new hinge-binding motifs for PI3K kinase inhibitors. A key reaction for the formation of 2 and 4 is the Hemmetsberger–Knittel cyclization of acryloazides. The core of 3 is accessible through reaction of an α-haloketone with 2-aminoimidazole.

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45

Wang, Xian-Feng, Min Chen, Li-Zhi Zhang, Zheng Zhao, and Chun-Long Yang. "Synthesis, characterization and bioactivity of novel 5,6-dihydropyrrolo[3,4-c]pyrazol-4- (1H)one derivatives." Heterocyclic Communications 21, no. 6 (December 1, 2015): 361–66. http://dx.doi.org/10.1515/hc-2015-0045.

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AbstractA series of novel 6-(sec-butyl)-3-methyl-1-(substituted phenyl)-5,6- dihydropyrrolo[3,4-c]pyrazol-4-(1H)ones 5a–h were synthesized using L-isoleucine methyl ester hydrochloride as the starting material. Their structures were characterized by 1H NMR, FT-IR, EI-MS and elemental analysis. Compound 5f was further analyzed by single-crystal X-ray diffraction. The bioassay results indicate that most of the compounds exhibit inhibitory activity against four plant pathogenic fungi Fusarium graminearum, Botrytis cinerea, Rhizoctonia cerealis and Colletotrichumcapsici.

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46

Bozorov, Kh A., N. Z. Mamadalieva, B. Zh Elmuradov, D. Triggiani, D. Egamberdieva, A. Tiezzi, H. A. Aisa, and Kh M. Shakhidoyatov. "Synthesis of Substituted Thieno[2,3-d]pyrimidin-4-ones and Their Testing for Evaluation of Cytotoxic Activity on Mammalian Cell Models." Journal of Chemistry 2013 (2013): 1–6. http://dx.doi.org/10.1155/2013/976715.

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From 2-amino-3-ethoxycarbonyl-4,5-dimethyl-, -polymethylenethiophenes (1-4) were synthesized 2,3-disubstituted thieno[2,3-d]dihydropyrrolo-, tetrahydropyrido-, and tetrahydroazepino[1,2-a]pyrimidin-4-ones (5-16) for pharmacological investigations. The 12 compounds (5-16) were individually evaluated for their antiproliferative activities on mammalian cancer cell models. All tested compounds showed weak affection on human cervix adenocarcinoma cells (HeLa) whereas some of the tested compounds exhibited more consistent inhibition of cell growth on murine myeloma cells (P3X). In both cases some compounds enhanced cell proliferation.

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47

Galeta, Juraj, Lukáš Tenora, Stanislav Man, and Milan Potáček. "Dihydropyrrolo[1,2-b]pyrazoles: withasomnine and related compounds." Tetrahedron 69, no. 34 (August 2013): 7139–46. http://dx.doi.org/10.1016/j.tet.2013.06.009.

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Nasrullayev, Azizbek O., Burkhon Zh Elmuradov, Kambarali K. Turgunov, Bakhodir Tashkhodjaev, and Khusnutdin M. Shakhidoyatov. "2,3-Dihydropyrrolo[2,1-b]quinazoline-9(1H)-thione." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (May 16, 2012): o1746. http://dx.doi.org/10.1107/s1600536812021228.

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In the crystal, molecules of the title compound, C11H10N2S, are connected by C—H...N interactions around threefold axes. Furthermore, they form stacks along the c axis showing π–π interactions between pyrimidine rings [centroid–centroid distance = 3.721 (1) Å]. The central ring is essentially planar with an r.m.s. deviation of 0.007 Å. The five-membered ring adopts an envelope conformation with the flap atom deviating by 0.241 (4) Å from the mean plane (r.m.s. deviation = 0.002 Å) through the other four ring atoms.

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49

Donghi, Monica, Silvia Pesci, Vincenzo Summa, Uwe Koch, Stephane Spieser, and Cristina Gardelli. "Regioselective Synthesis of 7,8-Dihydropyrrolo[1,2-a]pyrimidin-4(6H)-ones and 7,8-Dihydropyrrolo[1,2-a]pyrimidin-2(6H)-ones." Synlett 2010, no. 02 (December 11, 2009): 235–39. http://dx.doi.org/10.1055/s-0029-1218566.

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50

Winant, Pieterjan, Tomas Horsten, Shaiani Gil de Melo, Flavio Emery, and Wim Dehaen. "A Review of the Synthetic Strategies toward Dihydropyrrolo[1,2-a]Pyrazinones." Organics 2, no. 2 (June 4, 2021): 118–41. http://dx.doi.org/10.3390/org2020011.

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Dihydropyrrolo[1,2-a]pyrazinone rings are a class of heterocycles present in a wide range of bioactive natural products and analogues thereof. As a direct result of their bioactivity, the synthesis of this privileged class of compounds has been extensively studied. This review provides an overview of these synthetic pathways. The literature is covered up until 2020 and is organized according to the specific strategies used to construct the scaffold: fusing a pyrazinone to an existing pyrrole, employing a pyrazinone-first strategy, an array of multicomponent reactions and some miscellaneous reactions.

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