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

Venkatachalam Rajeshkumar; Chinnaraj Neelamegam; Sambandam Anandan

doi:10.1055/s-0039-1690024

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(21): 4023-4033
DOI: 10.1055/s-0039-1690024

paper

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

Venkatachalam Rajeshkumar ∗

Department of Chemistry, National Institute of Technology Tiruchirappalli, Tamil Nadu-620015, India eMail: orgrajeshkumar@gmail.com eMail: vrajesh@nitt.edu

,

Chinnaraj Neelamegam

,

Sambandam Anandan

› Institutsangaben

Abstract

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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.

Key words

metal-free synthesis - 1,4-enediones - 4-thioarylpyrroles - thiol-Michael reaction - C–S bond formation

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References

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Zusatzmaterial

Supporting Information