Journal
TETRAHEDRON LETTERS
Volume 49, Issue 27, Pages 4269-4271Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.04.146
Keywords
1,3-diarylpropenones; 2-aminothiophenol; 1,3-diaryl-2,3-dihydro-1,5-benzothiazepines; SDS; water; catalysis
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An efficient synthesis of 1,3-diaryl-2,3-dihydro-1,5-benzothiazepines has been developed by the reaction of various 1,3-diaryl-2-propenones with 2-aminothiophenol in water under neutral conditions catalysed by SDS. Excellent chemoselectivity was observed for substrates possessing halogen atoms or nitro/alkoxy/thioalkyl groups which did not undergo competitive aromatic nucleophilic substitution of the halogen atoms or the nitro group, reduction of the nitro or the a,p-unsaturated carbonyl group, or dealkylation of the alkoxy/thioalkoxy groups. (C) 2008 Elsevier Ltd. All rights reserved.
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