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Journal articles on the topic 'Synthesis of pyrroles'

Author: Grafiati

Published: 5 June 2025

Last updated: 15 July 2025

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1

Mohamed, Mosaad, Ramdan El-Domany, and Rania Abd El-Hameed. "Synthesis of certain pyrrole derivatives as antimicro-bial agents." Acta Pharmaceutica 59, no. 2 (2009): 145–58. http://dx.doi.org/10.2478/v10007-009-0016-9.

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Synthesis of certain pyrrole derivatives as antimicro-bial agentsIn an effort to establish new pyrroles and pyrrolo[2,3-d] pyrimidines with improved antimicrobial activity we report here the synthesis andin vitromicrobiological evaluation of a series of pyrrole derivatives. A series of new 2-aminopyrrole-3-carbonitriles (1a-d) were synthesized from the reaction of benzoin, primary aromatic amines and malononitrile, from which a number of pyrrole derivatives (2a-dto5a-d) and pyrrolo[2,3-d]pyrimidines (6a-dto10a, d) were synthesized. Thein vitroantimicrobial testing of the synthesized compounds

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2

Quiclet-Sire, Béatrice, and Samir Zard. "Convergent Routes to Pyrroles Exploiting the Unusual Radical Chemistry of Xanthates – An Overview." Synlett 28, no. 20 (2017): 2685–96. http://dx.doi.org/10.1055/s-0036-1590809.

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Convergent routes to a variety of pyrroles involving radical additions of xanthates are described. Emphasis is placed on reactions leading to the formation of 1,4-diketones or 1,4-ketoaldehydes or their synthetic equivalents, which can then be condensed with ammonia or primary amines in a variation of the classical Paal–Knorr synthesis of pyrroles. The modification of pyrroles by direct radical addition is also discussed.1 Introduction2 Earlier Routes to Pyrroles3 The Xanthate Radical Addition–Transfer Process4 Application to Pyrrole Synthesis5 Further Variations6 Direct Modification of Existi

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3

Iqbal, Sarosh, Hina Rasheed, Rabiya Javed Awan, Ramsha Javed Awan, Asma Mukhtar, and Mark G. Moloney. "Recent Advances in the Synthesis of Pyrroles." Current Organic Chemistry 24, no. 11 (2020): 1196–229. http://dx.doi.org/10.2174/1385272824999200528125651.

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: Pyrroles are the most prevalent heterocyclic compounds, which are present as the basic cores in many natural products, such as vitamin B12, bile pigments like bilirubin and biliverdin, the porphyrins of heme, chlorophyll, chlorins, bacteriochlorins, and porphyrinogens. The biological activities of compounds having pyrrole analogs include antimicrobial (antibacterial, antifungal), anti-cancer (anti-cytotoxic, antimitotic), anti-tumor, anti-hyperlipidemic, anti-depressant, anti-inflammatory, antihyperglycemic, antiproliferative, anti-HIV and anti-viral activities. Accordingly, significant atte

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4

Ta, Daniel D., Jeanne M. Favret, and Sergei V. Dzyuba. "Facile Synthesis of Pyrrolyl-Containing Semisquaraines in Water as Precursors for Non-Symmetric Squaraines." Compounds 3, no. 1 (2022): 17–26. http://dx.doi.org/10.3390/compounds3010002.

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One-step reactions between squaric acid and pyrroles, such as 3-ethyl-2,4-dimethyl-pyrrole and 1,2,5-trimethylpyrrole, in water provide the corresponding pyrrol-2-yl- and pyrrol-3-yl-containing semisquaraines in high yields. These semisquaraines serve as useful precursors for the synthesis of various non-symmetric pyrrole-containing squaraine dyes.

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5

Gao, Meng, Wenting Zhao, Hongyi Zhao, Ziyun Lin, Dongfeng Zhang, and Haihong Huang. "An efficient and facile access to highly functionalized pyrrole derivatives." Beilstein Journal of Organic Chemistry 14 (April 20, 2018): 884–90. http://dx.doi.org/10.3762/bjoc.14.75.

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A straightforward and one-pot synthesis of pyrrolo[3,4-c]pyrrole-1,3-diones via Ag(I)-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with N-alkyl maleimide, followed by readily complete oxidation with DDQ, has been successfully developed. Further transformation with alkylamine/sodium alkoxide alcohol solution conveniently afforded novel polysubstituted pyrroles in good to excellent yields. This methodology for highly functionalized pyrroles performed well over a broad scope of substrates. It is conceivable that this efficient construction method for privileged pyrrole scaffolds could

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6

Mateev, Emilio, Ali Irfan, Alexandrina Mateeva, Maya Georgieva, and Alexander Zlatkov. "Microwave-assisted organic synthesis of pyrroles (Review)." Pharmacia 71, no. () (2024): 1–10. https://doi.org/10.3897/pharmacia.71.e119866.

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The detection of pyrrole rings in numerous organic compounds with various pharmacological activities, emphasizes its huge importance in medicinal chemistry. Thus, the synthesis of pyrroles continues to arouse interest and Paal-Knorr condensation is considered to be the main synthetic route. A significant advance has been made since the MW activation was introduced in the organic synthesis which can be confirmed with the rapid growth of the published papers on that topic. Microwave irradiation is gaining popularity since faster reaction time, higher yields, easier work-up and reduced energy inp

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7

Menéndez, J., Marco Leonardi, Verónica Estévez, and Mercedes Villacampa. "The Hantzsch Pyrrole Synthesis: Non-conventional Variations and Applications of a Neglected Classical Reaction." Synthesis 51, no. 04 (2018): 816–28. http://dx.doi.org/10.1055/s-0037-1610320.

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Pyrrole is one of the most important one-ring heterocycles because of its widespread presence in natural products and unnatural bioactive compounds and drugs in clinical use. The preparation of pyrroles by reaction between primary amines, β-dicarbonyl compounds, and α-halo ketones, known as the Hantzsch pyrrole synthesis, is reviewed here for the first time. In spite of its age and its named reaction status, this method has received little attention in the literature. Recent work involving the use of non-conventional conditions has rejuvenated this classical reaction and this is emphasized in

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8

Miranda-Sánchez, Diter, Carlos H. Escalante, Dulce Andrade-Pavón, et al. "Pyrrole-Based Enaminones as Building Blocks for the Synthesis of Indolizines and Pyrrolo[1,2-a]pyrazines Showing Potent Antifungal Activity." Molecules 28, no. 20 (2023): 7223. http://dx.doi.org/10.3390/molecules28207223.

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As a new approach, pyrrolo[1,2-a]pyrazines were synthesized through the cyclization of 2-formylpyrrole-based enaminones in the presence of ammonium acetate. The enaminones were prepared with a straightforward method, reacting the corresponding alkyl 2-(2-formyl-1H-pyrrol-1-yl)acetates, 2-(2-formyl-1H-pyrrol-1-yl)acetonitrile, and 2-(2-formyl-1H-pyrrol-1-yl)acetophenones with DMFDMA. Analogous enaminones elaborated from alkyl (E)-3-(1H-pyrrol-2-yl)acrylates were treated with a Lewis acid to afford indolizines. The antifungal activity of the series of substituted pyrroles, pyrrole-based enaminon

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9

Palmieri, Alessandro, and Marino Petrini. "Synthesis and practical applications of 2-(2-nitroalkyl)pyrroles." Organic & Biomolecular Chemistry 18, no. 24 (2020): 4533–46. http://dx.doi.org/10.1039/d0ob00956c.

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Two main approaches can be designed for the synthesis of 2-(2-nitroalkyl)pyrroles using nitroalkenes or nitroalkanes in the reaction with pyrrole derivatives. The obtained nitroalkyl pyrroles can be converted into various bioactive compounds.

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10

Gharib, Ali, Manouchehr Jahangir, and J. Scheeren. "Novel catalytic method synthesis of calix[4]pyrroles using Preyssler and Wells-Dawson heteropolyacids." Polish Journal of Chemical Technology 13, no. 2 (2011): 70–73. http://dx.doi.org/10.2478/v10026-011-0027-4.

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Novel catalytic method synthesis of calix[4]pyrroles using Preyssler and Wells-Dawson heteropolyacids A catalytic synthesis of calix[4]pyrroles and N-confused calix[4]pyrroles by reaction of dialkyl or cycloalkyl ketones with pyrrole was performed using Preyssler, sodium30-tungsto pentaphosphate, [NaP5W30O110]14- and Wells-Dawson heteropolyacids as acidic catalysts. The process occurred under mild, eco-friendly and environmental friendly conditions and as a reusable, green catalyst at room temperature for 6 hours. The results showed that the yield for this synthesis is excellent with the use o

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11

Hotynchan, Andrii H., Olena M. Kovtun, and Yuriy P. Kovtun. "The Synthesis of Pyrroles from Nitroolefins." Journal of Organic and Pharmaceutical Chemistry 23, no. 2 (2025): 48–58. https://doi.org/10.24959/ophcj.25.323775.

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The synthesis of pyrroles occupies a key place in synthetic organic chemistry due to the numerous biological properties of pyrrole derivatives, in particular antimicrobial, antibacterial, antifungal, antimalarial, anticancer activities, etc. Therefore, pyrroles serve as building blocks in the creation of potential pharmaceuticals and also serve as the basis for the synthesis of boradipyrromethene dyes. One of the most well-known approaches to the synthesis of pyrroles is the reaction between nitroolefins, 1,3-dicarbonyl compounds, and amines, also known as the Grob-Camenisch reaction. This rev

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12

Mateev, Emilio, Ali Irfan, Alexandrina Mateeva, Maya Georgieva, and Alexander Zlatkov. "Microwave-assisted organic synthesis of pyrroles (Review)." Pharmacia 71 (March 25, 2024): 1–10. http://dx.doi.org/10.3897/pharmacia.71.e119866.

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The detection of pyrrole rings in numerous organic compounds with various pharmacological activities, emphasizes its huge importance in medicinal chemistry. Thus, the synthesis of pyrroles continues to arouse interest and Paal-Knorr condensation is considered to be the main synthetic route. A significant advance has been made since the MW activation was introduced in the organic synthesis which can be confirmed with the rapid growth of the published papers on that topic. Microwave irradiation is gaining popularity since faster reaction time, higher yields, easier work-up and reduced energy inp

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13

Kumar, Anil, Israr Ahmad, and M. Sudershan Rao. "Ytterbium(III) triflate catalyzed synthesis of calix[4]pyrroles in ionic liquids." Canadian Journal of Chemistry 86, no. 9 (2008): 899–902. http://dx.doi.org/10.1139/v08-121.

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Ytterbium(III) triflate has been utilized as a mild Lewis-acid catalyst for the synthesis of various calix[4]pyrroles by the condensation of pyrrole with different ketones in ionic liquids. The calix[4]pyrroles were obtained in high yield under ecofriendly, economical, and noncorrosive conditions, and the catalyst was recovered and recycled.Key words: calix[4]pyrrole, ionic liquid, ytterbium triflate.

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14

Safarov, Megli Djumayevich. "Technology for the production of disubstituted pyrroles." E3S Web of Conferences 410 (2023): 01019. http://dx.doi.org/10.1051/e3sconf/202341001019.

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In this work, we studied the catalytic synthesis of pyrrole and their derivatives from ketoximes and acetylene in the liquid phase under normal conditions in the presence of homogeneous catalysts. Mathematical modeling of the experiment was carried out using the Box-Wilson method and the optimal conditions for the synthesis of a number of pyrroles were found. The catalytic synthesis of pyrrole under vapor phase conditions in the presence of heterogeneous catalysts has been studied. Low-temperature polyfunctional catalysts have been developed that provide the highest yield of pyrroles.

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15

Shibata, Kotaro, Kotaro Shibata, Narendra N. Pati, and Yasuhide Inokuma. "Exploration of Synthesis and Coordination Chemistry of Thiazole-Containing Calix[3]Pyrroles." ECS Meeting Abstracts MA2024-01, no. 14 (2024): 1117. http://dx.doi.org/10.1149/ma2024-01141117mtgabs.

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Calix[n]pyrroles have been used as powerful and specific receptors and as extractants for anions and ion pairs over the past 20 years. In the recent past, calix[4]pyrroles have been used as systems that can move ions and ion pairs over lipophilic membranes [1]. Unfortunately, the coordination chemistry of calix[n]pyrroles hardly explored. The ring-contracted analog of calix[n]pyrrole, calix[3]pyrrole, was synthesized and recently published [2]. The structure of calix[3]pyrrole and its analogues is strained, and they show an appealing strain-induced ring expansion response. On the other hand, t

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16

Chen, Wenteng, Jiaan Shao, Zhi Li, Marc A. Giulianotti, and Yongping Yu. "Synthesis of 2,3,4-trisubstituted pyrroles via a facile reaction of vinyl azides and tosylmethyl isocyanide." Canadian Journal of Chemistry 90, no. 2 (2012): 214–21. http://dx.doi.org/10.1139/v11-150.

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A facile synthesis of polysubstituted pyrroles from tosylmethyl isocyanide (TOSMIC) and readily synthesized vinyl azides was developed. The reaction proceeded under mild conditions in the presence of base. 2-Tosyl-substituted pyrroles were obtained in moderate to good isolated yields. Additionally, a base-initiated one-pot pyrrole synthesis also was developed using carboxaldehydes, ethyl 2-azidoacetate, and TOSMIC.

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17

Krutošíková, Alžbeta, and Mikuláš Hanes. "Substituted 4-Benzylfuro[3,2-b]pyrroles." Collection of Czechoslovak Chemical Communications 57, no. 7 (1992): 1487–94. http://dx.doi.org/10.1135/cccc19921487.

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Preparation of 4-benzylfuro[3,2-b]pyrroles is described and their reactions with selected dienophiles are discussed. Utilization of 4-acetylfuro[3,2-b]pyrroles for preparation of 4-substituted derivatives of furo[3,2-b]pyrrole and the synthesis of ethyl 4-(2- and 4-nitrobenzyl)furo[3,2-b]pyrrole-5-carboxylates for fusing to a 1,4-diazepine system is presented.

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18

He, Yan-Hong, Gang-Qiang Wang, Ke-Ling Xu, and Zhi Guan. "An Efficient Procedure for the Synthesis of Polysubstituted Pyrroles in an Ionic Liquid." Zeitschrift für Naturforschung B 66, no. 2 (2011): 191–96. http://dx.doi.org/10.1515/znb-2011-0212.

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The ionic liquid 1-butyl-3-methyl-imidazolium hydrogen sulfate, [bmim]HSO4, was used as a catalyst and reaction medium for the pyrrole synthesis, and a wide range of aliphatic, aromatic, heteroaromatic and carboxylic 1,4-diketones easily underwent condensations with aniline and ethylenediamine to form polysubstituted pyrroles. Sequential decarboxylation/Paal-Knorr pyrrole condensation was observed, which provides a new and facile approach to monoester pyrroles from 1,4-diketo-2,3-dicarboxylic acid esters.

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19

Jux, Norbert, Daniel Gryko, Rafał Stężycki, David Reger, and Helen Hoelzel. "Synthesis and Photophysical Properties of Hexaphenylbenzene–Pyrrolo[3,2-b]pyrroles." Synlett 29, no. 19 (2018): 2529–34. http://dx.doi.org/10.1055/s-0037-1610286.

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Methods for the synthesis of pyrrolo[3,2-b]pyrroles containing hexaphenylbenzene moieties at the 2- and 5-positions or the 1- and 4-positions have been developed. It was shown that placing a hexaphenylbenzene moiety at the 2- and 5-positions requires a Diels–Alder reaction between an alkyne-substituted pyrrolopyrrole core and a 2,3,4,5-tetraphenylcyclopenta-2,4-dien-1-one. The resulting dyes show a strong blue fluorescence that was hypsochromically shifted by chlorination at the 3- and 6-positions. The overall conjugation between the hexaphenylbenzene moieties and the pyrrolopyrrole core is li

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20

Tejeswararao, D., and B. Srikanth. "SnCl2 Catalyzed Direct Synthesis of Pyrroles under Aqueous Conditions." Asian Journal of Chemistry 32, no. 4 (2020): 795–802. http://dx.doi.org/10.14233/ajchem.2020.22454.

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Synthetic substituted pyrroles are related with interesting biological activities, yet they remain inadequately explored within drug discovery. Late years have seen a growing interest in synthetic approaches that can provide access to structurally novel pyrroles so that the biological usefulness of this compound class can be more fully investigated. Herein, an efficient and versatile practical protocol for the pyrroles using stannous(II) chloride dihydrate as catalyst is described under aqueous conditions at 55 ºC in high yields. Also, this method is applicable for the preparation of diversity

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21

Reinus, Brandon, and Sean Kerwin. "A Copper-Catalyzed N-Alkynylation Route to 2-Substituted N-Alkynyl Pyrroles and Their Cyclization into Pyrrolo[2,1-c]oxazin-1-ones: A Formal Total Synthesis of Peramine." Synthesis 49, no. 11 (2017): 2544–54. http://dx.doi.org/10.1055/s-0036-1588736.

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Screening of a variety of ligands and reaction conditions for the copper-catalyzed cross-coupling of alkynyl bromides with pyrroles, reveals that the use of the phenanthroline ligand 4,7-dimethoxy-1,10-phenanthroline affords a range of ynpyrroles in good to moderate yields. Furthermore, the utility of these ynpyrroles is demonstrated in the preparation of a series of pyrrolo[2,1-c][1,4]oxazin-1-ones and a formal total synthesis of the pyrrole natural product peramine.

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22

More, Satish S., T. Krishna Mohan, Y. Sateesh Kumar, U. K. Syam Kumar, and Navin B. Patel. "Synthesis of novel 5-alkyl/aryl/heteroaryl substituted diethyl 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates by aziridine ring expansion of 2-[(aziridin-1-yl)-1-alkyl/aryl/heteroaryl-methylene]malonic acid diethyl esters." Beilstein Journal of Organic Chemistry 7 (June 20, 2011): 831–38. http://dx.doi.org/10.3762/bjoc.7.95.

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A novel synthetic methodology has been developed for the synthesis of diethyl 5-alkyl/aryl/heteroaryl substituted 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates (also called 2-substituted pyrroline-4,5-dihydro-3,3-dicarboxylic acid diethyl esters) by iodide ion induced ring expansion of 2-[(aziridin-1-yl)-1-alkyl/aryl/heteroaryl-methylene]malonic acid diethyl esters in very good to excellent yields under mild reaction conditions. The electronic and steric impact of the substituents on the kinetics of ring expansion of N-vinyl aziridines to pyrrolines has been studied. Various diversely substituted

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23

Medran, Noelia S., Agustina La-Venia, and Sebastian A. Testero. "Metal-mediated synthesis of pyrrolines." RSC Advances 9, no. 12 (2019): 6804–44. http://dx.doi.org/10.1039/c8ra10247c.

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The five-membered, nitrogen-containing pyrroline ring is a privileged structure. Pyrrolines—the dihydro derivatives of pyrroles—have three structural isomer classes: 1-, 2- and 3-pyrrolines. A review on metal-mediated synthesis of the three classes of pyrrolines is given.

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24

Cheng, Yukun, Channing K. Klein, and Ian A. Tonks. "Synthesis of pentasubstituted 2-aryl pyrroles from boryl and stannyl alkynes via one-pot sequential Ti-catalyzed [2 + 2 + 1] pyrrole synthesis/cross coupling reactions." Chemical Science 11, no. 37 (2020): 10236–42. http://dx.doi.org/10.1039/d0sc01576h.

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25

Krutošíková, Alžbeta. "Synthesis and reactions of condensed furan derivatives." Collection of Czechoslovak Chemical Communications 55, no. 3 (1990): 597–621. http://dx.doi.org/10.1135/cccc19900597.

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Synthesis of heterocyclic compounds containing a fused furan ring was studied. Substitution, addition and cycloaddition reactions of furo[3,2-b]pyrroles and their condensed derivatives involving the interesting transformations of furo[3,2-b]pyrrole system are presented.

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26

Gabrielli, Serena, Ludovica Ciabattoni, Susanna Sampaolesi, Roberto Ballini, and Alessandro Palmieri. "A new fully heterogeneous synthesis of pyrrole-2-acetic acid derivatives." RSC Advances 6, no. 50 (2016): 44341–44. http://dx.doi.org/10.1039/c6ra05348c.

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27

Xuan, Duc Dau. "Recent Progress in the Synthesis of Pyrroles." Current Organic Chemistry 24, no. 6 (2020): 622–57. http://dx.doi.org/10.2174/1385272824666200228121627.

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: Pyrrole derivatives are nitrogen-containing heterocyclic compounds and widely distributed in a large number of natural and non-natural compounds. These compounds possess a broad spectrum of biological activities such as anti-infammatory, antiviral, antitumor, antifungal, and antibacterial activities. Besides their biological activity, pyrrole derivatives have also been applied in various areas such as dyes, conducting polymers, organic semiconductors. : Due to such a wide range of applicability, access to this class of compounds has attracted intensive research interest. Various established

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28

Tian, Jun, Kang-Ning Yuan, Wen Liu, Hong-Hong Chang, Xing Li, and Wen-Chao Gao. "3-Thiolated pyrroles/pyrrolines: controllable synthesis and usage for the construction of thiolated fluorophores." Chemical Communications 57, no. 15 (2021): 1943–46. http://dx.doi.org/10.1039/d0cc07988j.

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29

Johnstone, Ken D., Wayne A. Pearce, and Simon M. Pyke. "Porphyrin building blocks: using a modified Barton-Zard approach to construct annulated pyrroles." Journal of Porphyrins and Phthalocyanines 06, no. 11 (2002): 661–72. http://dx.doi.org/10.1142/s1088424602000798.

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A modification of the Barton-Zard pyrrole synthesis involving condensation of isocyanoacetate esters with cyclic unsaturated sulfones using sodium hydride as base is demonstrated for the construction of annulated pyrroles.

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30

Salaheldin, Abdellatif M. "Enaminonitriles in Heterocyclic Synthesis: Novel Synthesis of 3-Aminopyrroles and Pyrrolo[3,2-d]pyrimidine Derivatives." Zeitschrift für Naturforschung B 63, no. 5 (2008): 564–70. http://dx.doi.org/10.1515/znb-2008-0514.

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Several new 3-aminopyrrole derivatives have been synthesized from 3-substituted amino-2-phenylacrylonitriles using Thorpe-Ziegler cyclization. These substituted pyrroles are readily converted into 5H-pyrrolo[3,2-d]pyrimidines (9-deazapurines).

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Singh, Dileep Kumar, and Rajesh Kumar. "Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach." Beilstein Journal of Organic Chemistry 19 (June 27, 2023): 928–55. http://dx.doi.org/10.3762/bjoc.19.71.

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Pyrrole is an important aromatic heterocyclic scaffold found in many natural products and predominantly used in pharmaceuticals. Continuous efforts are being made to design and synthesize various pyrrole derivatives using different synthetic procedures. Among them, the Clauson–Kaas reaction is a very old and well-known method for synthesizing a large number of N-substituted pyrroles. In recent years, due to global warming and environmental concern, research laboratories and pharmaceutical industries around the world are searching for more environmentally friendly reaction conditions for synthe

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32

Sobenina, Lyubov, Elena Sagitova, Igor Ushakov, and Boris Trofimov. "Transition-Metal-Free Synthesis of Pyrrolo[1,2-a]pyrazines via Intramolecular Cyclization of N-Propargyl(pyrrolyl)enaminones." Synthesis 49, no. 17 (2017): 4065–81. http://dx.doi.org/10.1055/s-0036-1588454.

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A concise transition-metal-free strategy for the synthesis of pyrrolo[1,2-a]pyrazines with enone substituents has been developed. It includes the following key steps: (a) cross-coupling of pyrroles with acyl(bromo)acetylenes in solid alumina at room temperature to give 2-(acylethynyl)pyrroles; (b) addition of propargylamine to the above acetylenes to form the corresponding N-propargylenaminones; and (c) chemo- and stereoselective base-catalyzed (Cs2CO3/DMSO) intramolecular cyclization of the synthesized propargylic derivatives to form (acylmethylidene)pyrrolo[1,2-a]pyrazines of Z-configuratio

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33

Ivanov, Andrey V., Svetlana V. Martynovskaya, Victoria S. Shcherbakova, et al. "Ambient access to a new family of pyrrole-fused pyrazine nitrones via 2-carbonyl-N-allenylpyrroles." Organic Chemistry Frontiers 7, no. 24 (2020): 4019–25. http://dx.doi.org/10.1039/d0qo00762e.

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The chemo-, regio- and stereoselective synthesis of pyrrole-fused pyrazine nitrones via the direct reaction of 2-carbonyl-N-allenylpyrroles (readily accessible from the corresponding NH-pyrroles) with hydroxyl amine hydrochloride has been developed.

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Bobošík, Vladimír, and Alžbeta Krutošíková. "Synthesis of N-Phenylsulfonyl Protected Furo[3,2-b]pyrroles." Collection of Czechoslovak Chemical Communications 59, no. 2 (1994): 499–502. http://dx.doi.org/10.1135/cccc19940499.

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Protection of nitrogen atom of heterocyclic molecules, such as indole and pyrrole types, enables various reactions of these systems. N-Phenylsulfonyl derivatives, which have been widely used for this purpose, were prepared in the indole series by the reaction of N-sodium and N-lithium salts with benzenesulfonyl chloride. This method requires waterfree and oxygenfree conditions. On the other hand, the phase transfer catalysis conditions used in this work obviates these disadvantages. We therefore selected the latter method for the preparation of variously substituted 4-phenylsulfonylfuro[3,2-b]

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35

Beh, Michael H. R., Carlotta Figliola, Kate-Lyn A. R. Lund, et al. "Regioselective substituent effects upon the synthesis of dipyrrins from 2-formyl pyrroles." Canadian Journal of Chemistry 96, no. 7 (2018): 779–84. http://dx.doi.org/10.1139/cjc-2017-0662.

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The synthesis of symmetric α-free meso-H-dipyrrin hydrobromides from 5-H-2-formyl pyrroles was investigated. The self-condensation produces regioisomeric dipyrrins through adoption of two mechanistic pathways. The key difference between the two pathways lies in which position of the pyrrole directs nucleophilic attack. Through a systematic study involving various substituted and (or) isotopically labelled 5-H-2-formyl pyrroles, we herein provide evidence to suggest that not only do two mechanistic pathways exist, but the steric bulk of the substituent adjacent to the 5-unsubstituted position i

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36

Kucukdisli, Murat, Dorota Ferenc, Marcel Heinz, Christine Wiebe, and Till Opatz. "Simple two-step synthesis of 2,4-disubstituted pyrroles and 3,5-disubstituted pyrrole-2-carbonitriles from enones." Beilstein Journal of Organic Chemistry 10 (February 24, 2014): 466–70. http://dx.doi.org/10.3762/bjoc.10.44.

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The cyclocondensation of enones with aminoacetonitrile furnishes 3,4-dihydro-2H-pyrrole-2-carbonitriles which can be readily converted to 2,4-disubstituted pyrroles by microwave-induced dehydrocyanation. Alternatively, oxidation of the intermediates produces 3,5-disubstituted pyrrole-2-carbonitriles.

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37

Aldoshin, Alexander S., Andrey A. Tabolin, Sema L. Ioffe та Valentine G. Nenajdenko. "An Easy Synthesis of Monofluorinated Derivatives of Pyrroles from β-Fluoro-β-Nitrostyrenes". Molecules 26, № 12 (2021): 3515. http://dx.doi.org/10.3390/molecules26123515.

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The catalyst-free conjugate addition of pyrroles to β-Fluoro-β-nitrostyrenes was investigated. The reaction was found to proceed under solvent-free conditions to form 2-(2-Fluoro-2-nitro-1-arylethyl)-1H-pyrroles. The effectiveness of this approach was demonstrated through the preparation of a series of the target products in a quantitative yield. The kinetics of a conjugate addition of pyrrole was studied in detail to reveal the substituent effect and activation parameters of the reaction. The subsequent base-induced elimination of nitrous acid afforded a series of novel 2-(2-Fluoro-1-arylviny

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38

Silaichev, Pavel S., Lidia N. Dianova, Tetyana V. Beryozkina, Vera S. Berseneva, Andrey N. Maslivets, and Vasiliy A. Bakulev. "Synthesis of Non-Aromatic Pyrroles Based on the Reaction of Carbonyl Derivatives of Acetylene with 3,3-Diaminoacrylonitriles." Molecules 28, no. 8 (2023): 3576. http://dx.doi.org/10.3390/molecules28083576.

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The reaction of 3,3-diaminoacrylonitriles with DMAD and 1,2-dibenzoylacetylene was studied. It is shown that the direction of the reaction depends on the structure both of acetylene and of diaminoacrylonitrile. In the reaction of DMAD with acrylonitriles bearing a monosubstituted amidine group, 1-substituted 5-amino-2-oxo-pyrrole-3(2H)ylidenes are formed. On the other hand, a similar reaction of acrylonitriles containing the N,N-dialkylamidine group affords 1-NH-5-aminopyrroles. In both cases, pyrroles containing two exocyclic double bonds are formed in high yields. A radically different type

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39

Edukondalu, Athukuri, Sandip Sambhaji Vagh, Ting-Han Lin, and Wenwei Lin. "Construction of indeno[1,2-b]pyrroles via chemoselective N-acylation/cyclization/Wittig reaction sequence." Chemical Communications 57, no. 16 (2021): 2045–48. http://dx.doi.org/10.1039/d0cc08184a.

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An unprecedented chemoselective N-acylation/cyclization/Wittig reaction sequence for the efficient synthesis of indeno[1,2-b]pyrroles and rearranged indeno[1,2-b]pyrrole derivatives is demonstrated, employing phosphorus zwitterions, acyl chlorides and Et<sub>3</sub>N.

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40

Martyn, Derek C., та Andrew D. Abell. "The Synthesis and Testing of α-(Hydroxymethyl)pyrroles as DNA Binding Agents". Australian Journal of Chemistry 57, № 11 (2004): 1073. http://dx.doi.org/10.1071/ch04183.

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The α-(hydroxymethyl)pyrroles 16a and 16b were prepared and shown to be cytotoxic against the P388 cancer cell line. Ethyl 5-hydroxymethyl-1H-pyrrole-2-carboxylate 18 was inactive, demonstrating that an α-(hydroxymethyl)pyrrole group alone is not sufficient for activity. Compound 16b has been shown to bind to DNA with reasonable affinity.

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41

Shen, Jinhai, Xifa Yang, Fuyuan Wang, Yue Wang, Guolin Cheng та Xiuling Cui. "Base-mediated regiospecific cascade synthesis of N-(2-pyridyl)pyrroles from N-propargylic β-enaminones". RSC Advances 6, № 54 (2016): 48905–9. http://dx.doi.org/10.1039/c6ra08987a.

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42

Sharifian Anari, Mahdieh, and Farahnaz K. Behbahani. "Four components synthesis of 1,2,3,4-tetrasubstituted pyrroles using iron (iii) phosphate as a green activator." Lebanese Science Journal 18, no. 2 (2017): 219–25. http://dx.doi.org/10.22453/lsj-018.2.219-225.

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A simple synthesis of 1,2,3,4-tetrasubstituted pyrrole derivatives is reported from the reaction of aromatic aldehydes, β–dicarbonyl compounds, amines and nitromethane in the presence of iron (III) phosphate under reflux conditions. The use of iron (III) phosphate as a green activator, mild reaction conditions and synthesis of some unprecedented tetrasubstituted pyrroles are the features of this protocol.

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43

Guo, Tenglong, Quanbin Jiang, and Zhengkun Yu. "Palladium-catalyzed oxidative annulation of in situ generated enones to pyrroles: a concise route to functionalized indoles." Organic Chemistry Frontiers 2, no. 10 (2015): 1361–65. http://dx.doi.org/10.1039/c5qo00203f.

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Pd(ii)-catalyzed, Cu(ii)-mediated indole synthesis from pyrroles and 3-chloropropiophenones has been efficiently achieved. In-situ generated enones were employed for the establishment of a benzene ring onto a pyrrole backbone via dehydrochlorination/C–H olefination/cycloaddition/dehydrogenative aromatization.

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44

Cui, Keli, Meng Gao, Hongyi Zhao, Dongfeng Zhang, Hong Yan, and Haihong Huang. "An Efficient Synthesis of Aryl-Substituted Pyrroles by the Suzuki–Miyaura Coupling Reaction of SEM-Protected Pyrroles." Molecules 24, no. 8 (2019): 1594. http://dx.doi.org/10.3390/molecules24081594.

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An efficient arylation of SEM-protected pyrroles by the Suzuki–Miyaura coupling reaction has been developed. The reaction can be carried out under mild conditions to provide aryl-substituted pyrroles in moderate to excellent yields. The scope and limitations of the methodology were evaluated, and the reaction was tolerant of a wide range of functionalities. Compared to the reported methods, the protocol has some advantages, such as commercially available materials, no debrominated by-products being formed, and the amine-protecting group being stable under the reaction conditions. The synthetic

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45

Trofimov, Boris A., Maxim D. Gotsko, Ivan V. Saliy, Lyubov N. Sobenina, Igor A. Ushakov, and Victoriya V. Kireeva. "Functionalized Bipyrroles and Pyrrolyl-Aminopyrones from Acylethynylpyrroles and Diethyl Aminomalonate." Synthesis 54, no. 04 (2021): 1134–44. http://dx.doi.org/10.1055/a-1681-4164.

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AbstractAn efficient method for the synthesis of 1H,1′H-2,3′-bipyrroles (up to 72% yield) by the cyclocondensation of easily available 2-(acylethynyl)pyrroles with diethyl aminomalonate hydrochloride has been developed. The reaction proceeds under reflux in MeCN (6 h) in the presence of Cs2CO3. Under the same conditions, 2-(acylethynyl)pyrroles with bulky (benzyl and octyl) substituents at nitrogen atom react with diethyl aminomalonate to afford 1H,2′H-2,3′-bipyrroles and pyrrolyl-aminopyrones.

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46

Gotsko, Maxim D., Ivan V. Saliy, Igor A. Ushakov, Lyubov N. Sobenina, and Boris A. Trofimov. "Substituent-Dependent Divergent Synthesis of 2-(3-Amino-2,4-dicyanophenyl)pyrroles, Pyrrolyldienols and 3-Amino-1-acylethylidene-2-cyanopyrrolizines via Reaction of Acylethynylpyrroles with Malononitrile." Molecules 27, no. 23 (2022): 8528. http://dx.doi.org/10.3390/molecules27238528.

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An efficient method for the synthesis of pharmaceutically and high-tech prospective 2-(3-amino-2,4-dicyanophenyl)pyrroles (in up to 88% yield) via the reaction of easily available substituted acylethynylpyrroles with malononitrile has been developed. The reaction proceeds in the KOH/MeCN system at 0 °C for 2 h. In the case of 2-acylethynylpyrroles without substituents in the pyrrole ring, the reaction changes direction: instead of the target 2-(3-amino-2,4-dicyanophenyl)pyrroles, the unexpected formation of pyrrolyldienols and products of their intramolecular cyclization, 3-amino-1-acylethylid

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47

Ferreira, Joana R. M., Raquel Nunes da Silva, João Rocha, Artur M. S. Silva, and Samuel Guieu. "1,2,4-Triphenylpyrroles: Synthesis, Structure and Luminescence Properties." Synlett 31, no. 06 (2020): 632–34. http://dx.doi.org/10.1055/s-0039-1690828.

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Pyrroles are widely found in natural products and play an important role in biological processes. Certain pyrrole derivatives are fluorescent and may be used as molecular probes or biomarkers in the diagnosis of diseases, such as Alzheimer’s or Parkinson’s. Herein is reported the synthesis of five new pyrrole derivatives bearing phenyl rings on positions 1, 2, and 4, with electron-donating groups at the periphery. The introduction of more or stronger electron-donating groups red-shifts and increases the efficiency of the fluorescence emission.

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48

Gribble, G. W. "Novel chemistry of indole in the synthesis of heterocycles." Pure and Applied Chemistry 75, no. 10 (2003): 1417–32. http://dx.doi.org/10.1351/pac200375101417.

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Indoles that are substituted at the 2- or 3-position with electron-withdrawing groups (nitro, phenylsulfonyl) undergo nucleophilic addition, 1,3-dipolar cycloaddition, and Diels–Alder reactions to give a variety of indoles, pyrroloindoles, and carbazoles. New methods for the synthesis of furo[3,4-b]indoles and the novel ring system furo[3,4-b]pyrrole are described for the first time. Diels–Alder reactions of furo[3,4-b]pyrroles afford indoles after dehydration of the primary cycloadducts. Efficient syntheses of both 2- and 3-nitroindoles from indole are reported, and the first generation and s

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49

Anderson, Hugh J., and Charles E. Loader. "The Synthesis of 3-Substituted Pyrroles from Pyrrole." Synthesis 1985, no. 04 (1985): 353–64. http://dx.doi.org/10.1055/s-1985-31211.

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50

Kotthireddy, Kavitha *. and Pasula Aparna. "AN EFFICIENT ONE-POT SYNTHESIS OF COUMARIN-PYRROLE HYBRID COMPOUNDS UNDER ENVIRONMENTALLY HARMLESS CONDITIONS." Journal of Scientific Research in Pharmacy 7, no. 1 (2018): 10–12. https://doi.org/10.5281/zenodo.1161768.

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<strong><em>ABSTRACT</em></strong> <strong><em>C</em></strong><em>oumarin and pyrrole heterocyclics have found to show diversified biological activities. Due to their easy availability and stability they applied in various branches of science. Based on this point of view coumarin-pyrrole hybrid compounds have been synthesized in a one-pot three-component method.  Ammonium acetate (NH<sub>4</sub>OAc) has been found to be an efficient regent and catalyst for this method of synthesis under purely eco-friendly conditions. We have successfully demonstrated the triple role of ammonium acetate a

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