Solid state synthesis of 2-aroylbenzo[b]furans, 1,3-thiazoles and 3-aryl-5,6-dihydroimidazo[2,1-b][1,3]thiazoles from α-tosyloxyketones using microwave irradiation †
- 1 January 1998
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 24,p. 4093-4096
- https://doi.org/10.1039/a807563h
Abstract
The expeditious solventless syntheses of 2-aroylbenzo[b]furans, 1,3-thiazoles and 3-aryl-5,6-dihydroimidazo[2,1-b][1,3]thiazoles are described from readily accessible α-tosyloxyketones and mineral oxides in processes that are accelerated by exposure to microwaves. The 2-aroylbenzo[b]furans are readily obtained from salicylaldehydes and α-tosyloxyketones in the presence of solid potassium fluoride doped alumina (KF–Al2O3) whereas montmorillonite K-10 clay provides 1,3-thiazoles from thioamides and α-tosyloxyketones. Similarly, ethylenethiourea and α-tosyloxyketones provide bridgehead nitrogen heterocycles, 3-aryl-5,6-dihydroimidazo[2,1-b][1,3]thiazoles, in excellent yields which are not easily obtainable under classical heating conditions.Keywords
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