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Issue 6, 2012
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InCl3 catalyzed domino route to 2H-chromene-2-ones via [4 + 2] annulation of 2-hydroxyarylaldehydes with α-oxoketene dithioacetal under solvent-free conditions

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Abstract

A facile and efficient synthesis of 3-aroyl/heteroaroyl/ferrocenoyl/alkanoyl-2H-chromen-2-ones has been developed by the cyclocondensation of α-oxoketene dithioacetals and 2-hydroxyarylaldehydes catalyzed by InCl3 under solvent-free conditions. No co-catalyst or activator is needed and MeSH is the only by-product of this protocol. The methodology involves ring annulation of 2-hydroxyarylaldehydes with a variety of α-oxoketene dithioacetals offering rapid entry into differentially substituted chromen-2-ones. The condensation of ferrocene derived α-oxoketene dithioacetal and 2-hydroxyarylaldehyde furnished coumarin installed on a ferrocene platform.

Graphical abstract: InCl3 catalyzed domino route to 2H-chromene-2-ones via [4 + 2] annulation of 2-hydroxyarylaldehydes with α-oxoketene dithioacetal under solvent-free conditions

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Supplementary files

Article information


Submitted
31 Oct 2011
Accepted
07 Dec 2011
First published
01 Feb 2012

RSC Adv., 2012,2, 2413-2421
Article type
Paper

InCl3 catalyzed domino route to 2H-chromene-2-ones via [4 + 2] annulation of 2-hydroxyarylaldehydes with α-oxoketene dithioacetal under solvent-free conditions

R. K. Verma, G. K. Verma, G. Shukla and M. S. Singh, RSC Adv., 2012, 2, 2413
DOI: 10.1039/C2RA00987K

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