One-Pot Synthesis of Pentasubstituted Pyrroles from Propargylic Alcohols, Amines, and Dialkyl Acetylenedicarboxylates; Tandem Amination, Propargylation and Cycloisomerization Catalyzed by Molecular Iodine

Nisith Bhunia; Biswanath Das

doi:10.1055/s-0032-1318485

Synthesis, Table of Contents

Synthesis 2013; 45(8): 1045-1050
DOI: 10.1055/s-0032-1318485

paper

One-Pot Synthesis of Pentasubstituted Pyrroles from Propargylic Alcohols, Amines, and Dialkyl Acetylenedicarboxylates; Tandem Amination, Propargylation and Cycloisomerization Catalyzed by Molecular Iodine^{[
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Nisith Bhunia

Organic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad 500 007, India Fax: +91(40)27193198 Email: biswanathdas@yahoo.com

,

Biswanath Das*

Organic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad 500 007, India Fax: +91(40)27193198 Email: biswanathdas@yahoo.com

› Author Affiliations

Abstract

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Abstract

A multicomponent one-pot synthesis of fully substituted pyrroles has been developed by the tandem reaction of amines, dialkyl acetylenedicarboxylates, and propargylic alcohols using iodine as a catalyst. The reaction was complete in three hours and afforded the products in high yields (75–88%). The method is simple, efficient, cost-effective, and metal-free.

Key words

pentasubstituted pyrrole - tandem reaction - iodine - metal-free synthesis

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References

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Supplementary Material

Supporting Information

One-Pot Synthesis of Pentasubstituted Pyrroles from Propargylic Alcohols, Amines, and Dialkyl Acetylenedicarboxylates; Tandem Amination, Propargylation and Cycloisomerization Catalyzed by Molecular Iodine[ 1 ]

One-Pot Synthesis of Pentasubstituted Pyrroles from Propargylic Alcohols, Amines, and Dialkyl Acetylenedicarboxylates; Tandem Amination, Propargylation and Cycloisomerization Catalyzed by Molecular Iodine^{[
¹
]}