Hydrazine-mediated one-pot amination-oxidation reaction: facile synthesis of 4-amino-. beta.-carbolines and 4-aminoisoquinolines

ML Trudell, N Fukada, JM Cook

Index: Trudell, Mark L.; Fukada, N.; Cook, J. M. Journal of Organic Chemistry, 1987 , vol. 52, # 19 p. 4293 - 4296

Full Text: HTML

Citation Number: 21

Abstract

The conversion of the 4-oxo-2-benzoyl-1, 2, 3, 4-tetrahydro-(3-carbolines la and lb, respectively, into their corresponding 4-amino-(3-carbolines 2a and 2b was effected in 70% yield in refluxing hydrazine. In contrast, phenylhydrazine, when heated with the 4-oxo derivative lb, gave the pyridodiindole 18a. This compound derives its origin from an initial Fischer indole cyclization, followed by loss of the 2-benzoyl group and aromatization to ...