New method for the synthesis of 8-azasteroids: Synthesis of benzo[<i>a</i>]cyclohexa[<i>f</i>]furo[2,3-<i>g</i>]quinolizines from 2-cinnamoylcyclohexa[<i>b</i>]oxirane

Abstract

The reaction of 2-cinnamoylcyclohexa[b]oxirane with allylamine gave cis-2(β),3,4a,5,6,7,8,8a(β)-octahydro-1-allyl-4a(β)-hydroxy-(2α)-phenylquinolin-4-one, which upon subsequent reaction with dimethyl malonate, peroxide epoxidation, and heating with hydrochloric acid gave cis-4,5,6a(β),7,8,9,10a-octahydro-6-allyl-20-oxo-5(α)-phenyl-3-chlorofuro[3,2-d]quinoline. Heating of this intermediate in 96% sulfuric acid gave trans-3a(a),7a(a),9,10(β),14b(α),15-hexahydro-10(α)-methyl-2-oxo-1-chlorobenzo[a]cyclohexa[f]furo[2,3-g]quinolizine.

How to Cite
Pshenichnyi, G. V. Chem. Heterocycl. Compd. 1994, 30, 361. [Khim. Geterotsikl. Soedin. 1994, 411.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01165707