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Synlett 2023; 34(16): 1930-1938
DOI: 10.1055/a-2113-2981
DOI: 10.1055/a-2113-2981
letter
An Efficient One-Pot, Three-Component Synthesis of Tetrasubstituted Pyrroles under Catalyst- and Solvent-Free Conditions
Financial support from the Science and Engineering Research Board (SERB) for the award of a research grant (CRG/2021/006424) and Department of Science and Technology (DST), Ministry of Science and Technology, India, Fund for Improvement of S&T Infrastructure in Universities and Higher Educational Institutions (FIST, SR/FST/CS-I/2018/62) to SCBT, SASTRA Deemed University for the NMR facility are gratefully acknowledged.
Abstract
An environmentally benign, catalyst- and solvent-free, three-component synthesis of tetrasubstituted pyrroles was established. The reaction proceeds via a nucleophilic attack of primary amine on dialkyl acetylenedicarboxylate followed by Michael addition with β-nitrostyrene and successive intramolecular cyclization and aromatization to yield 1,2,3,4-tetrasubstituted pyrroles in good to excellent yields. A wide range of primary amines including aromatic amines and benzylamines were coupled with differently substituted β-nitrostyrenes and dialkyl acetylenedicarboxylate. Furthermore, compared to previous reported methods, the present study is highly atom economical and environmentally benign and can be scaled up.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2113-2981.
- Supporting Information
Publication History
Received: 04 May 2023
Accepted after revision: 20 June 2023
Accepted Manuscript online:
21 June 2023
Article published online:
11 August 2023
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