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Paper | Regular issue | Vol 63, No. 8, 2004, pp.1813-1819
Published online, 8th June, 2004
DOI: 10.3987/COM-04-10099
Novel Synthesis of 3-Substituted Derivatives of (Alkyliden-1-yl)-3H-benzo[b]thiophen-2-ones

Sukanta Kamila and Edward R. Biehl*

*Chemistry Department, Southern Methodist University, Dallas, TX 75275-0314, U.S.A.

Abstract

The reaction of 2-methylthiophenol with sodium hydride and N,N-diethylcarbamyl chloride in THF afforded N,N-diethylthiocarbamic acid S-o-tolyl ester in 97% yield. The ester was subsequently treated with LDA and various aromatic aldehydes to provide new 3-substituted derivatives of (alkyliden-1-yl)-3H-benzo[b]thiophen-2-ones. The Z isomer was formed as major product with smaller amounts of the E isomer. The structure of (Z)-3-(thiophen-2-yl)methylidenyl-3H-benzo[b]thiophen-2-one was confirmed by X-Ray crystallography.