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-octa-hydro-6-allyl-20-oxo-5(α)phenyl-3-chlorofuro[3,2-d]quinoline. Heating of this intermediate in 96% sulfuric acid gavetrans-3a(a),7a(a),9,10(β),14b(α),15-hexahydro-10(α)-methyl-2-oxo-1-chlorobenzo[a]cyclo-hexa[f]furo[2,3-g]quitiolizine.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
F. A. Lakhvich, L. G. Lis, and A. A. Akhrem, Usp. Khim.,53, 1014 (1984).
G. V. Pshenichnyi, V. A. Mashenkov, and L. S. Stanishevskii, Vestn. Belorussk. Univ., Ser. 2, No. 1, 66 (1987).
T. V. Baranovskaya, G. V. Pshenichnyi, and L. S. Stanishevskii, Vestn. Belorussk. Univ., Ser. 2, No. 3, 12 (1992).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 30, No. 3, pp. 411–414, March, 1994.
Rights and permissions
About this article
Cite this article
Pshenichnyi, G.V. New method for the synthesis of 8-azasteroids: Synthesis of benzo[a]cyclohexa[f]furo[2,3-g]-quinolizines from 2-cinnamoylcyclohexa[b]oxirane. Chem Heterocycl Compd 30, 361–364 (1994). https://doi.org/10.1007/BF01165707
Issue Date:
DOI: https://doi.org/10.1007/BF01165707