Synthesis 2019; 51(21): 4023-4033
DOI: 10.1055/s-0039-1690024
paper
© Georg Thieme Verlag Stuttgart · New York

An Expedient, Direct, Three-Component Approach for the Synthesis of 4-Thioarylpyrroles

Department of Chemistry, National Institute of Technology Tiruchirappalli, Tamil Nadu-620015, India   Email: orgrajeshkumar@gmail.com   Email: vrajesh@nitt.edu
,
Chinnaraj Neelamegam
,
Sambandam Anandan
› Author Affiliations
We thank the Department of Science and Technology (DST), New Delhi, India for the financial support for this work under a DST-INSPIRE faculty scheme (DST/INSPIRE/04/2016/000295).
Further Information

Publication History

Received: 24 June 2019

Accepted after revision: 20 July 2019

Publication Date:
15 August 2019 (eFirst)

Abstract

A three-component strategy for the synthesis of 4-thioarylpyrroles from 1,4-enediones, thiols, and ammonium formate in one-pot has been developed. The reaction proceeds through the sequential thiol-Michael/Paal–Knorr reaction of 1,4-enediones with the formation of one new C–S and two C–N bonds. The operationally simple protocol provides direct access to the highly functionalized 4-thioarylpyrroles with free-NH in good to excellent yields. The synthetic application of resulting 4-thioarylpyrroles was demonstrated by oxidation of the sulfur atom to the corresponding sulfoxide and sulfone.

Supporting Information

 
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