Conformationally restricted tricyclic antidepressants. 1. Octahydrodibenzazepinonaphthyridines as rigid imipramine analogs

…, GW Peng, RC Speth, HI Yamamura…

Index: Martin, Arnold R.; Paradkar, Vidyadhar M.; Peng, Geoffrey W.; Speth, Robert C.; Yamamura, Henry I.; Horn, Alan S. Journal of Medicinal Chemistry, 1980 , vol. 23, # 8 p. 865 - 873

Full Text: HTML

Citation Number: 18

Abstract

The stereoselective synthesis and structure elucidation of the racemic 2-methyl-l, 2, 3, 4, 4a, 8, 9, 15a-octahydro-l5H-dibenz [b, flazepino [5, 4a, 4-bc]-2, 7-naphthyridine ring-fusion isomers (la and lb) are described. Photocyclization of N-(l-methyl-l, 2, 5, 6- tetrahydronicotinyl)-lO, ll-dihydro-5H-dibenzazepine (3) in methanol vs. tetrahydrofuran stereoselectively gave, respectively, the cis (moderate yield) or the trans (poor yield) ...