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Synthesis 2002(7): 0875-0878
DOI: 10.1055/s-2002-28523
PAPER
© Georg Thieme Verlag Stuttgart · New York

One-Step Synthesis of Thioaurones

M. Grazia Cabiddu, Salvatore Cabiddu*, Enzo Cadoni, Stefania De Montis, Claudia Fattuoni, Stefana Melis, Michele Usai
Dipartimento di Scienze Chimiche, Università degli Studi di Cagliari, Cittadella Universitaria di Monserrato, SS 554 Bivio per Sestu, 09042 Monserrato (CA), Italy
Fax: +39(70)6754388; e-Mail: scabiddu@unica.it;
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Publication History

Received 7 November 2001
Publication Date:
14 May 2002 (online)

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Abstract

A rapid, one-step preparation of 2-(arylmethylidene)-1-benzothiophen-3-ones (thioaurones) using directed α-metallation, ring closure and aldol-type condensation is described. The reaction leads exclusively to the Z-isomer.

Key words

benzothiophenes - cyclizations - carbanions - metalations - stereoselectivity

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