Literature DB >> 32980995

Revisit to the synthesis of 1,2,3,4-tetrasubstituted pyrrole derivatives in lactic acid media as a green solvent and catalyst.

Dilek Akbaslar1, E Sultan Giray2, Oztekin Algul3.   

Abstract

In this study, for the first time, lactic acid was used as a bio-based green catalyst and reaction medium for the synthesis of 1,2,3,4-tetrasubstituted pyrrole derivatives from one-pot three-component reaction of commercially available primary amines, 1,3-dicarbonyl compounds, and trans-β-nitrostyrene at room temperature. Thirty-three corresponding pyrroles, of which eight are novel and have been reported for the first time, were synthesized in high to excellent yields in lactic acid media and characterized by spectroscopic analysis. In all examined cases, lactic acid represented many advantages, including shorter reaction time, ease of product isolation, higher yields, no by-products, no chromatographic process, and lower volatility in the reaction. This bio-based green solvent can also be recycled and reused three times without loss of its efficiency as a catalyst and solvent.
© 2020. Springer Nature Switzerland AG.

Entities:  

Keywords:  Green synthesis; Lactic acid; Multicomponent reaction; Tetrasubstituted pyrroles

Mesh:

Substances:

Year:  2020        PMID: 32980995     DOI: 10.1007/s11030-020-10122-1

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  23 in total

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Journal:  J Org Chem       Date:  2000-04-21       Impact factor: 4.354

3.  Potential antitumor agents. 59. Structure-activity relationships for 2-phenylbenzimidazole-4-carboxamides, a new class of "minimal" DNA-intercalating agents which may not act via topoisomerase II.

Authors:  W A Denny; G W Rewcastle; B C Baguley
Journal:  J Med Chem       Date:  1990-02       Impact factor: 7.446

Review 4.  Synthesis of isoindoles and related iso-condensed heteroaromatic pyrroles.

Authors:  Thomas S A Heugebaert; Bart I Roman; Christian V Stevens
Journal:  Chem Soc Rev       Date:  2012-07-10       Impact factor: 54.564

5.  Synthesis and biological activity of 2-anilino-4-(1H-pyrrol-3-yl) pyrimidine CDK inhibitors.

Authors:  Shudong Wang; Gavin Wood; Christopher Meades; Gary Griffiths; Carol Midgley; Iain McNae; Campbell McInnes; Sian Anderson; Wayne Jackson; Mokdad Mezna; Rhoda Yuill; Malcolm Walkinshaw; Peter M Fischer
Journal:  Bioorg Med Chem Lett       Date:  2004-08-16       Impact factor: 2.823

Review 6.  Lamellarins and related pyrrole-derived alkaloids from marine organisms.

Authors:  Hui Fan; Jiangnan Peng; Mark T Hamann; Jin-Feng Hu
Journal:  Chem Rev       Date:  2007-12-21       Impact factor: 60.622

7.  Regioselective preparation of 2-substituted 3,4-diaryl pyrroles: a concise total synthesis of ningalin B.

Authors:  James L Bullington; Russell R Wolff; Paul F Jackson
Journal:  J Org Chem       Date:  2002-12-27       Impact factor: 4.354

Review 8.  Sunitinib: a multitargeted receptor tyrosine kinase inhibitor in the era of molecular cancer therapies.

Authors:  Georgios S Papaetis; Kostas N Syrigos
Journal:  BioDrugs       Date:  2009       Impact factor: 5.807

Review 9.  Pyrrole: An emerging scaffold for construction of valuable therapeutic agents.

Authors:  Somnath S Gholap
Journal:  Eur J Med Chem       Date:  2015-12-13       Impact factor: 6.514

10.  An improved kilogram-scale preparation of atorvastatin calcium.

Authors:  Yuri V Novozhilov; Mikhail V Dorogov; Maria V Blumina; Alexey V Smirnov; Mikhail Krasavin
Journal:  Chem Cent J       Date:  2015-02-13       Impact factor: 4.215

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