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Paper | Regular issue | Vol 34, No. 1, 1992, pp.61-66
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5847
Reactions of 3-Formylindole N,N-Dimethylhydrazones with Dienophiles. A Stereospecific Addition

Salvador Escrivá Moscardó, José Sepúlveda-Arques,* Belén Abarca Gonzalez, Rafael Ballesteros Campos, Concepción Soriano Soto, Santiago García Granda, and Fermín Gomez Beltran

*Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Valencia, Valencia, Spain

Abstract

3-Formyl-1-methylindole N,N-dimethylhydrazone (1a) and 3-formylindole N,N-dimethylhydrazone (1b) react with methyl propiolate to give 3-cyano-1-methylindole (2a) and 3-cyanoindole (2b) respectively. When dimethyl acetylenedicarboxylate was used as a reagent the hydrazone (1a) afforded the nitrile (2a) and the pyridine (3) but in the reaction of the hydrazone (1b) an enantiomeric mixture of R,R and S,S dimethyl 1-(3-cyano-1-indolyl)-2-dimethylaminosuccinates (4) were obtained and their structures confirmed by X-ray single crystal analysis.