Alum-Catalyzed Synthesis of 3-(1H-Pyrrol-2-yl)-2H-chromen-2-ones: A Water–PEG 400 Binary Solvent Mediated, One-Pot, Three-Component Protocol

Gargi Pal; Sanjay Paul; Asish R. Das

doi:10.1055/s-0032-1318494

Synthesis, Table of Contents

Synthesis 2013; 45(9): 1191-1200
DOI: 10.1055/s-0032-1318494

paper

Alum-Catalyzed Synthesis of 3-(1H-Pyrrol-2-yl)-2H-chromen-2-ones: A Water–PEG 400 Binary Solvent Mediated, One-Pot, Three-Component Protocol

Authors

Gargi Pal

Department of Chemistry, University of Calcutta, Kolkata 700009, India Fax: +91(33)23519754 Email: ardchem@caluniv.ac.in Email: ardas66@rediffmail.com
Sanjay Paul

Department of Chemistry, University of Calcutta, Kolkata 700009, India Fax: +91(33)23519754 Email: ardchem@caluniv.ac.in Email: ardas66@rediffmail.com
Asish R. Das*

Department of Chemistry, University of Calcutta, Kolkata 700009, India Fax: +91(33)23519754 Email: ardchem@caluniv.ac.in Email: ardas66@rediffmail.com

Abstract

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Abstract

A novel, one-pot, three-component condensation reaction of 3-(bromoacetyl)coumarin, acetylacetone, and an amine using the inexpensive, environmentally benign, and mild catalyst alum as an efficient catalyst and the water–PEG 400 binary solvent system gives 3-(1-aryl-4-acetyl-5-methyl-1H-pyrrol-2-yl)-2H-chromen-2-ones, a new heterocyclic scaffold containing both the coumarin and pyrrole nuclei in a single molecule, in good to excellent yields. This methodology offers several advantages: simple procedure, excellent yields, short reaction times, and green aspects such as avoiding toxic catalysts and solvents.

Key words

pyrrole derivatives - coumarin - alum - binary solvent - green protocol

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References

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Supplementary Material

Supporting Information (PDF)