CONDENSED ISOQUINOLINES. 10. BOROHYDRIDE REDUCTION IN THE 5H-ISOQUINO[2,3-<i>a</i>]QUINAZOLIN-5-ONE SERIES

Abstract

Borohydride reduction in a series of 7-benzyl- and newly synthesized 7-arylmethylene-7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones leads stereoselectively to erythro-7-benzyl-6,6a,7,12-tetrahydro-5H-isoquino[2,3-a]quinazolin-5-ones. 7,7-Disubstituted 7,12-dihydro-5H-isoquino[2,3-a]-quinazolin-5-ones are inert to the action of sodium borohydride, but spiro[5H-isoquino[2,3-a]quinazolin-7(12H),2'-indan]-5-one is reduced under rigid conditions to 6,6a-dihydrospiro[5H-isoquino[2,3-a]quinazolin-7(12H),2'-indan]-5-one. 7-Acetyl- and 7-benzoyl-6,11-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones are converted in an aqueous alcoholic solution of sodium borohydride to the previously described 6,6a,7,12-tetrahydro-5H-isoquino[2,3-a]quinazolin-5-one. The structure and special features of the conformational behavior of the reduction products obtained were demonstrated by ¹H NMR spectroscopy.

How to Cite
Kisel, V. M.; Potikha, L. M.; Turov, A. V.; Kovtunenko, V. A. Chem. Heterocycl. Compd. 2001, 37, 1153. [Khim. Geterotsikl. Soedin. 2001, 1258.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1013296120225