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Communication | Regular issue | Vol 23, No. 9, 1985, pp.2221-2224
Published online, 1st January, 1970
DOI: 10.3987/R-1985-09-2221
Reaction of 3-Acylindoles with Diethyl Phosphorocyanidate. A Facile Synthesis of 2-Cyano-3-indoleacetonitriles

Takushi Kurihara,* Mitsuko Hayakawa, Takeo Wakita, and Shinya Harusawa

*Faculty of Pharmaceutical Science, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan

Abstract

3-Acylindoles (1,7a-7d) were easily converted into 2-cyano-3-indoleacetonitriles (5,9a-9d) by treatment with diethyl phosphorocyanidate in the presence of lithium cyanide in excellent yields. Treatment of 9a with acetylenic esters in the presence of sodium hydride in tetrahydrofuran afforded 1-amino-4-cyanocarbazoles (10a and 10b). The compound 9a also reacted with benzyne in the presence of lithium di-isopropylamide to give 6-amino-11-cyano-5-methylbenzo[b]carbazole (11) in 64% yield, together with a small amount of 6,11-o-benzenobenzo[b]carbazole (12).