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Journal articles on the topic 'Pyrrole Synthesis'

Author: Grafiati

Published: 11 December 2022

Last updated: 25 January 2023

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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 (June 1, 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 was carried out against Gram-positive, Gram-negative bacteria and fungi. Some of the prepared compounds, [2-amino-1-(2-methylphenyl)-4,5-diphenyl-1H-pyrrole-3-carbonitriles (1b), 2-amino-3-carbamoyl-1-(3-methylphenyl)-4,5-diphenyl-1H-pyrroles (2b),N-(3-cyano-1-(2-methylphenyl)-4,5-diphenyl-1H-pyrrol-2-yl)-acetamides (3b),N-(3-cyano-1-(3-methylphenyl)-4,5-diphenyl-1H-pyrrol-2-yl)-acetamides (3c), 2-amino-1-(4-methoxyphenyl)-4,5-diphenyl-3-tetrazolo-1H-pyrroles (5d),7-(4-methoxyphenyl)-5,6-diphenyl-7H-pyrrolo [2,3-d]pyrimidin-4(3H)-ones (7d), 7-(3-methylphenyl)-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-thione (9b) andN-(7-(2-methylphenyl)-5,6-diphenyl-7H-pyrrolo[2,3-d] pyrimidine)-N-aryl amines (10a)] showed potent antimicrobial activity.

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2

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 (December 28, 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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3

Quiclet-Sire, Béatrice, and Samir Zard. "Convergent Routes to Pyrroles Exploiting the Unusual Radical Chemistry of Xanthates – An Overview." Synlett 28, no. 20 (July 21, 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 Existing Pyrrole Rings7 Outlook and Perspectives

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4

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 (December 3, 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 this review. Some applications of the Hantzsch reaction in target-oriented synthesis are also discussed.1 Introduction2 The Conventional Hantzsch Pyrrole Synthesis3 Hantzsch Pyrrole Synthesis under Non-conventional Conditions4 Applications of the Hantzsch Pyrrole Synthesis5 Conclusions

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5

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 (September 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 attention has been paid to develop competent methods for the synthesis of pyrroles with improved yields in short times. This review gives an overview of different methods for the synthesis of pyrrole using easily available precursors using the following routes. . Synthesis of monosubstituted pyrrole using 2,5-dimethoxyfuran . Synthesis of pyrrole using dialkylacetylene dicarboxylate . Synthesis of pyrroles using β-ketoester . Synthesis of pyrrole using 1,2-dicarbonyl compounds . Synthesis of pyrroles using 1,3-dicarbonyl compounds . Synthesis of pyrroles using 1,3-dicarbonyl, amine, nitro and aldehyde group . Synthesis of pyrroles using 1,4-dicarbonyl compound and amines . Synthesis of pyrrole using enones . Synthesis of pyrroles using moieties having acetylene group

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6

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 deliver more active compounds for medicinal chemistry research.

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7

Chen, Fang, Parveen Akhtar, Leon A. P. Kane-Maguire, and Gordon G. Wallace. "Synthesis and Characterization of Chiral Conducting Polymers Based on Polypyrrole." Australian Journal of Chemistry 50, no. 9 (1997): 939. http://dx.doi.org/10.1071/c96189.

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A range of optically active pyrrole monomers have been synthesized in which a chiral sub- stituent is covalently bonded either to the pyrrole N or C3 ring position, namely (–)-(1R)-4-methyl-N-(1-phenylethyl)pyrrole-3-carboxamide, (+)-(1S)-4-methyl-N-(1-phenylethyl)pyrrole-3-carboxamide, (–)-(1R)-4-methyl-N-(1-naphthylethyl)pyrrole-3-carboxamide, (+)-(1S)-4-methyl-N-(1-naphthylethyl)pyrrole-3-carboxamide, (+)-(2S)-2-(1H-pyrrol-1-yl)propionic acid, (+)-(1S)-N-(1-phenyl-ethyl)pyrrole, and (–)-(1R)-N-(1-phenylethyl)pyrrole. Their chiroptical properties have been established by circular dichroism spectroscopy. Electropolymerization of the three N-substituted pyrrole monomers provided films of chiral conducting polymers, whose electrical and spectroscopic properties are described. Although oxidation of the C3 substituted pyrrole monomers was also facile, electrodeposition was poor and films of the associated polymers could not be obtained.

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8

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 (September 1, 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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9

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 (March 14, 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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10

Portilla Zuniga, Omar Miguel, Angel Gabriel Sathicq, Jose Jobanny Martinez Zambrano, and Gustavo Pablo Romanelli. "Green Synthesis of Pyrrole Derivatives." Current Organic Synthesis 14, no. 6 (September 28, 2017): 865–82. http://dx.doi.org/10.2174/1570179414666161206124318.

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Background: Pyrroles are organic cyclic compounds with an extensive and fascinating chemistry. These compounds have a wide structural variety and they are an important basis in technological development as they can be used as drugs, dyes, catalysts, pesticides, etc. Therefore, the production of these heterocyclic compounds by efficient clean methodologies is a great achievement in contemporary chemistry. In this paper, we show recent green procedures in the synthesis of pyrrole derivatives such as Hantzsch, Knorr and Paal- Knorr syntheses, as well as new eco-friendly synthetic procedures with high efficiency and low environmental impact. Objective: This work focusses on the recent advances in the pyrrole synthesis using clean techniques like ultrasound (US), microwaves (MW), high speed vibration milling (HSVM), catalysts use, solvent replace and other methodologies applied to common reactions to obtain the pyrrole core which follow the green chemistry principles. Conclusion: The main challenge of Green Chemistry is to gradually eliminate the generation of hazardous or harmful materials or replace them with less toxic and safer ones. However, this process must be driven by scientific developments. Its application in the synthesis of heterocyclic compounds such as pyrrole derivatives involves multiple economic and social benefits due to the biological importance of these compounds and their direct impact on the pharmaceutical industry. Although many processes are still under investigation using novel methodologies of green activation such as microwaves, ultrasound and HSVM, as well as synthetic processes in continuous flow and processes at room temperature, promising results such as cost and waste reduction and greater efficiency are achieved.

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11

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 (September 26, 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 limited, as evident from their photophysical properties. The hexaphenylbenzene moieties attached to the pyrrolo[3,2-b]pyrrole core could not be transformed into hexa-peri-hexabenzocoronenes through intramolecular oxidative aromatic coupling.

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12

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 (February 1, 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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13

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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14

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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15

Pravardhan Reddy, E., A. Sumankumar, B. Sridhar, Y. Hemasri, Y. Jayaprakash Rao, and B. V. Subba Reddy. "1,5-Electrocyclization of conjugated azomethine ylides derived from 3-formyl chromene and N-alkyl amino acids/esters." Organic & Biomolecular Chemistry 15, no. 36 (2017): 7580–83. http://dx.doi.org/10.1039/c7ob00705a.

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A novel strategy has been developed for the synthesis of chromeno[3,4-b]pyrrol-4(3H)-one and substituted pyrrole derivatives. This is the first example of the preparation of highly substituted pyrrole derivatives from chromene-3-carboxaldehydes.

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16

Yu, Qixin, Xiaoyu Li, Xinyue Wang, and Jianhui Liu. "Regioselective Synthesis of 2,5-Disubstituted Pyrroles via Stepwise Iododesilylation and Coupling Reactions." Australian Journal of Chemistry 71, no. 3 (2018): 95. http://dx.doi.org/10.1071/ch17341.

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A new protocol has been developed for the regioselective preparation of 2,5-disubstituted pyrroles. This approach is based on a stepwise iododesilylation and a subsequent coupling reaction, involving a 6-step pathway starting from the simplest pyrrole. A variety of 2,5-disubstituted pyrrole derivatives are accessible in moderate to good yields. In this study, the protection group for the pyrrole nitrogen is carefully chosen and N,N-dimethylaminosulfonyl is the final choice, which facilitates the subsequent double lithiation and makes the pyrrole moiety more stable. However, the attempted removal of this group fails under several different conditions. Instead, unexpected dimethylaminosulfonyl migration to the β-position of the pyrrole ring in the presence of tetrabutylammonium fluoride is observed.

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17

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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18

Xuan, Duc Dau. "Recent Progress in the Synthesis of Pyrroles." Current Organic Chemistry 24, no. 6 (May 25, 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 synthetic methods such as Paal-Knorr, Huisgen, and Hantzsch have been modified and improved. In addition, numerous novel methods for pyrrole synthesis have been discovered. This review will focus on considerable studies on the synthesis of pyrroles, which date back from 2014.

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19

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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20

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 novel pyrroline derivatives have been synthesized by this methodology and the products can be used as key intermediates in the synthesis of substituted pyrrolines, pyrroles and pyrrolidines.

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21

Martyn, Derek C., and Andrew D. Abell. "The Synthesis and Testing of α-(Hydroxymethyl)pyrroles as DNA Binding Agents." Australian Journal of Chemistry 57, no. 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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22

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 (February 13, 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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23

Philkhana, Satish Chandra, Fatimat O. Badmus, Isaac C. Dos Reis, and Rendy Kartika. "Recent Advancements in Pyrrole Synthesis." Synthesis 53, no. 09 (March 17, 2021): 1531–55. http://dx.doi.org/10.1055/s-0040-1706713.

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AbstractThis review article features selected examples on the synthesis of functionalized pyrroles that were reported between 2014 and 2019. Pyrrole is an important nitrogen-containing aromatic heterocycle that can be found in numerous compounds of biological and material significance. Given its vast importance, pyrrole continues to be an attractive target for the development of new synthetic reactions. The contents of this article are organized by the starting materials, which can be broadly classified into four different types: substrates bearing π-systems, substrates bearing carbonyl and other polar groups, and substrates bearing heterocyclic motifs. Brief discussions on plausible reaction mechanisms for most transformations are also presented.1 Introduction2 From π-Systems2.1 Alkenes2.2 1,6-Dienes2.3 Allenes2.4 Alkynes2.5 Propargylic Groups2.6 Homopropargylic Amines3 From Carbonyl Compounds3.1 Aldehydes3.2 Ketones3.3 Cyanides and Isocyanides3.4 Formamides3.5 β-Enamines3.6 Dicarbonyl Compounds4 From Polar Compounds4.1 Aminols4.2 Diols4.3 Organonitro Compounds5 From Heterocycles5.1 Münchnones5.2 Isoxazoles5.3 Carbohydrates5.4 trans-4-Hydroxy-l-prolines5.5 Pyrrolines6 Summary

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24

Macías, Mario A., Juan-Carlos Castillo, and Jaime Portilla. "A series of (E)-5-(arylideneamino)-1-tert-butyl-1H-pyrrole-3-carbonitriles and their reduction products to secondary amines: syntheses and X-ray structural studies." Acta Crystallographica Section C Structural Chemistry 74, no. 1 (January 1, 2018): 82–93. http://dx.doi.org/10.1107/s2053229617017260.

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An efficent access to a series of N-(pyrrol-2-yl)amines, namely (E)-1-tert-butyl-5-[(4-chlorobenzylidene)amino]-1H-pyrrole-3-carbonitrile, C16H16ClN3, (7a), (E)-1-tert-butyl-5-[(2,4-dichlorobenzylidene)amino]-1H-pyrrole-3-carbonitrile, C16H15Cl2N3, (7b), (E)-1-tert-butyl-5-[(pyridin-4-ylmethylene)amino]-1H-pyrrole-3-carbonitrile, C15H16N4, (7c), 1-tert-butyl-5-[(4-chlorobenzyl)amino]-1H-pyrrole-3-carbonitrile, C16H18ClN3, (8a), and 1-tert-butyl-5-[(2,4-dichlorobenzyl)amino]-1H-pyrrole-3-carbonitrile, C16H17Cl2N3, (8b), by a two-step synthesis sequence (solvent-free condensation and reduction) starting from 5-amino-1-tert-butyl-1H-pyrrole-3-carbonitrile is described. The syntheses proceed via isolated N-(pyrrol-2-yl)imines, which are also key synthetic intermediates of other valuable compounds. The crystal structures of the reduced compounds showed a reduction in the symmetry compared with the corresponding precursors, viz. Pbcm to P\overline{1} from compound (7a) to (8a) and P21/c to P\overline{1} from compound (7b) to (8b), probably due to a severe change in the molecular conformations, resulting in the loss of planarity observed in the nonreduced compounds. In all of the crystals, the supramolecular assembly is controlled mainly by strong (N,C)—H...N hydrogen bonds. However, in the case of (7a)–(7c), C—H...Cl interactions are strong enough to help in the three-dimensional architecture, as observed in Hirshfeld surface maps.

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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

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 (February 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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27

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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28

Sollert, Carina, Daniel Kocsi, Reuben T. Jane, Andreas Orthaber, and K. Eszter Borbas. "C-glycosylated pyrroles and their application in dipyrromethane and porphyrin synthesis." Journal of Porphyrins and Phthalocyanines 25, no. 07n08 (June 23, 2021): 741–55. http://dx.doi.org/10.1142/s1088424621500723.

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Pyrrole C-glycosylated in either the 2- or the 3-position could be prepared by the acid-catalyzed reaction between trichloroacetimidate glycosyl donors and pyrrole, or [Formula: see text]-phenyl-tri?uoroacetimidate glucosyl donor and [Formula: see text]-TIPS pyrrole, respectively. Pyrroles carrying glucose, mannose, galactose and lactose in the 2-position, and glucose in the 3-position were obtained. The configurations of the products could be assigned using a combination of 1D and 2D NMR spectroscopy. A number of undesired background reactions yielding a variety of stereo- and regioisomers were identified; in several cases these could be eliminated. Glycosylpyrroles could be incorporated into mono- and diglycosylated dipyrromethanes, a diglycosylated BODIPY dye, and a monoglycosylated Zn(II) porphyrin without damaging the sugar unit.

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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 (November 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

Davis, Rohan A., Anthony R. Carroll, and Ronald J. Quinn. "The Synthesis of Two Combinatorial Libraries Using a 4-(2-Thienyl)-pyrrole Template." Australian Journal of Chemistry 55, no. 12 (2002): 789. http://dx.doi.org/10.1071/ch02110.

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The synthesis of the novel biaryl compound, 4-(2-thienyl)-1H-pyrrole-2-carbaldehyde (1), by Suzuki–Miyaura coupling conditions is reported. Compound (1) was subsequently used as a combinatorial template in the parallel solution-phase synthesis of an amine and imine compound library. The amine library was produced using reductive amination conditions, and purification was achieved by a liquid–liquid partition followed by silica chromatography to afford ten amine analogues. The imine library consisted of five compounds, which were synthesized using volatile primary amines that allowed purification by evaporation. The synthesis of the novel and related biaryl carbaldehyde, tert-butyl-2-(5-formyl-1H-pyrrol-3-yl)-1H-pyrrole-1-carboxylate (2) is also reported.

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31

Mai, Huyen Le Thi, Nhung Thanh Thi Truong, Thiet Quoc Nguyen, Bao Kim Doan, Dat Hung Tran, Le-Thu T. Nguyen, Woosung Lee, et al. "Synthesis and characterization of donor–acceptor semiconducting polymers containing 4-(4-((2-ethylhexyl)oxy)phenyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrole for organic solar cells." New Journal of Chemistry 44, no. 39 (2020): 16900–16912. http://dx.doi.org/10.1039/d0nj02616f.

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D–A polymers containing 4-(4-((2-ethylhexyl)oxy)phenyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrole and 2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione were successfully synthesized and applied for organic solar cells.

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32

Ivanov, Andrey V., Svetlana V. Martynovskaya, Victoria S. Shcherbakova, Igor A. Ushakov, Tatyana N. Borodina, Alexander S. Bobkov, and Nadezhda M. Vitkovskaya. "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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33

Abell, AD, and JC Litten. "Synthesis and Amino Acid Chain Extension of 1-Acylated Hydroxymethylpyrroles." Australian Journal of Chemistry 46, no. 10 (1993): 1473. http://dx.doi.org/10.1071/ch9931473.

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Acylation of pyrrole-2-carbaldehyde (3) with an N-phthaloyl amino acid chloride, N,N-diisopropylethylamine and 4-dimethylaminopyridine (dmap) gave the 1-acylpyrrole-2-carbalde-hydes (4a-c). The 1-acylated pyrroles (4d-i), (8) and (9) were similarly prepared in good yields from the relevant pyrrole derivative using dmap and either an acid chloride/N,N- diisopropylethylamine or an anhydride/triethylamine. Reduction of (4a-f) with zinc borohydride gave the 1-acylated hydroxymethylpyrroles (5a-f). A coupling of (5a) with N-Cbz-L-Val-L-Val-OH under Mitsunobu conditions gave the tetrapeptide analogue (11).

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34

Kerr, Daniel J., and Bernard L. Flynn. "Studies Towards a Concise Enantioselective Synthesis of Roseophilins." Australian Journal of Chemistry 68, no. 12 (2015): 1821. http://dx.doi.org/10.1071/ch15407.

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An oxazolidone auxiliary-controlled asymmetric Nazarov reaction has been applied to the synthesis of the cyclopentyl-fused pyrrole core of roseophilins. Additionally, a concise synthetic route to the pyrrole-furan biaryl fragment required in the synthesis of the recently isolated dechlororoseophilin is described. It is anticipated that these two syntheses can be combined in future efforts to provide efficient, convergent access to (+)-dechlororoseophilin.

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35

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

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36

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 (January 1, 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 of Preyssler and Wells-Dawson type tungstophosphoric heteropolyacid, H6[P2W18O62], catalysts. The synthesis reaction of calix[4]pyrroles and N-confused calix[4]pyrroles was developed using different solvents and the best yields were obtained in chloroform.

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37

A. A. Elbannany, Araf, and Laila I. Ibrahim. "Synthesis of Pyrrole, Pyrrolidone, Pyrrolo[3,4-c]pyrazole, Pyrrolo[3,2-b]pyridine and Pyrrolo[3,2-b]pyrrole Derivatives." HETEROCYCLES 27, no. 9 (1988): 2071. http://dx.doi.org/10.3987/com-88-4628.

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38

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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39

Kadushkin, A. V., T. V. Stezhko, and V. G. Granik. "New synthesis of pyrrolo[1,2-a] pyrrole derivatives." Chemistry of Heterocyclic Compounds 22, no. 4 (April 1986): 466–67. http://dx.doi.org/10.1007/bf00542796.

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40

Janiga, Anita, Dominika Bednarska, Bjarne Thorsted, Jonathan Brewer, and Daniel T. Gryko. "Quadrupolar, emission-tunable π-expanded 1,4-dihydropyrrolo[3,2-b]pyrroles – synthesis and optical properties." Org. Biomol. Chem. 12, no. 18 (2014): 2874–81. http://dx.doi.org/10.1039/c4ob00143e.

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A–D–A chromophores containing pyrrolo[3,2-b]pyrrole, as a central donor moiety, display blue, turquoise, yellow and orange fluorescence, depending on the strength of the electron-withdrawing substituent.

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41

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 Et₃N.

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42

Gribble, G. W. "Novel chemistry of indole in the synthesis of heterocycles." Pure and Applied Chemistry 75, no. 10 (January 1, 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 successful electrophilic trapping of a 2,3-dilithioindole has been achieved.

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43

Sharma, Ritambhara, Vellanki Lakshmi, Tamal Chatterjee, and Mangalampalli Ravikanth. "Effects of five membered aromatic heterocycles at the meso-position on the electronic properties of 3-pyrrolyl BODIPY." New Journal of Chemistry 40, no. 7 (2016): 5855–60. http://dx.doi.org/10.1039/c6nj00118a.

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44

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 (December 27, 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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45

Tejeswararao, D., and B. Srikanth. "SnCl2 Catalyzed Direct Synthesis of Pyrroles under Aqueous Conditions." Asian Journal of Chemistry 32, no. 4 (February 25, 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 and oriented pyrrole derivatives.

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46

A. A. Elbannany, Araf, Afaf A. A. Elbannany, and Laila I. Ibrahim. "Synthesis of Pyrrole, Pyrrolo[3,4-b]pyridine and Pyrrplo[3,2-b]pyridine Derivatives." HETEROCYCLES 26, no. 9 (1987): 2323. http://dx.doi.org/10.3987/r-1987-09-2323.

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47

Pawar, Amol Prakash, Jyothi Yadav, Nisar Ahmad Mir, Eldhose Iype, Krishnan Rangan, Sumati Anthal, Rajni Kant, and Indresh Kumar. "Direct catalytic synthesis of β-(C3)-substituted pyrroles: a complementary addition to the Paal–Knorr reaction." Chemical Communications 57, no. 2 (2021): 251–54. http://dx.doi.org/10.1039/d0cc06357f.

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Direct catalytic multicomponent synthesis of β-(C3)-substituted pyrroles is developed with good to high yields, using aqueous succinaldehyde, primary amines, and isatins under mild conditions. An access to the β-substituted free NH-pyrrole is the main focus of the work along with DFT-calculations.

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48

Huang, Wenbo, Kaimei Wang, Ping Liu, Minghao Li, Shaoyong Ke, and Yanlong Gu. "Three-component reactions of aromatic amines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal to access N-(hetero)aryl-4,5-unsubstituted pyrroles." Beilstein Journal of Organic Chemistry 16 (November 30, 2020): 2920–28. http://dx.doi.org/10.3762/bjoc.16.241.

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N-(Hetero)aryl-4,5-unsubstituted pyrroles were synthesized from (hetero)arylamines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal by using aluminum(III) chloride as a Lewis acid catalyst through [1 + 2 + 2] annulation. This new versatile methodology provides a wide scope for the synthesis of different functional N-(hetero)aryl-4,5-unsubstituted pyrrole scaffolds, which can be further derived to access multisubstituted pyrrole-3-carboxamides. In the presence of 1.2 equiv of KI, a polysubstituted pyrazolo[3,4-b]pyridine derivative was also successfully synthesized.

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49

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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50

Guo, Chang, Bin Sun, and Yuning Li. "Synthesis and properties of pyrrolo[3,4-c]pyrrole-1,3-dione based polymer semiconductors and their performance in organic thin film transistors." Polym. Chem. 5, no. 18 (2014): 5247–54. http://dx.doi.org/10.1039/c4py00372a.

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