NEW SYNTHESIS OF 3H-BENZO[B]THIOPHEN-2-ONES

$1,050P41FY2009RRNIH

Washington University, Saint Louis MO

Investigators

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Abstract

This subproject is one of many research subprojects utilizing the resources provided by a Center grant funded by NIH/NCRR. The subproject and investigator (PI) may have received primary funding from another NIH source, and thus could be represented in other CRISP entries. The institution listed is for the Center, which is not necessarily the institution for the investigator. The reaction of 2-methylthiophenol with sodium hydride and N,N-diethylcarbamoyl chloride in THF afforded N,N-diethylthiocarbamic acid S-o-tolyl ester in good yield. The ester was subsequently treated with LDA and various arom. aldehydes to provide 3-substituted derivatives of (alkyliden-1-yl)-3H-benzo[b]thiophen-2-ones, e.g., I. The Z isomer was formed as major product with smaller amounts of the E isomer. The structure of (Z)-3-(thiophen-2-yl)methyl-idenyl-3H-benzo[b]thiophen-2-one was confirmed by X-Ray crystallography.

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