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Paper | Regular issue | Vol 27, No. 2, 1988, pp.453-456
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4391
Condensed Heteroaromatic Ring Systems. XIV. Cyclization of ortho-Substituted α-Ethoxynnamates to Some Heteroaromatics

Takao Sakamaoto, Yoshinori Kondo, and Hiroshi Yamanaka*

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

The reaction of 2-iodoaniline with ethyl 2-ethoxyacrylate in the presence of palladium-charcoal gave 3-ethoxy-2(1H)-quinolinone, and the reaction of 2-iodoacetanilide with the same reagent yielded ethyl 2-acetylamino-α-ethoxycinnamate which was cyclized to ethyl indole-2-carboxylate under acidic conditions. On the other hand, the palladium-catalyzed reaction of 2-iodobenzonitrile and ethyl 2-iodobenzoate afforded the corresponding cinnamates which were transformed into isoquinoline and isocoumarin derivatives.