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Communication | Regular issue | Vol 19, No. 8, 1982, pp.1367-1370
Published online, 1st January, 1970
DOI: 10.3987/R-1982-08-1367
Condensation of 2-Hydroxytryptamine with Dimethyl 4-Ethyl-4-formylpimelane

Esahak Ali, Pulak K. Chakraborty, and Satyesh C. Pakrashi

*Indian Institute of Chemical Biology, Calcutta-700 032, India

Abstract

Condensation of 2-hydroxytryptamine (1) with dimethyl 4-ethyl-4-fomylpimelate (2) yielded the stereoisomeric oxindoles, 8A, 8B, 8C, and 8D which were separated and their stereochemistry assigned. The compounds 8A-D or their N-methyl derivatives, 5A-D could be selectively reduced to the oxindole-amines 9 or 3 by treatment with phosphorus oxychloride followed by sodium borohydride but the amines were isomerised under the reaction condition.