ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis and conformation of 5,6,7,8-tetrahydrodibenz[c,e]azocine

F. Szemes, A. Rybár, D. Uhrín, and E. Solčániová

Drug Research Institute, CS-90001 Modra

Abstract: A simplified four- or alternatively five-step synthesis of 5,6,7,8-tetrahydrodibenz[c,e]azocine from phenanthrene is described. The latter was ozonolyzed to the known 3,8-dimethoxydibenzo[c,e][1,2]dioxacyclooctane, which, when treated with alkylamine and nitromethane afforded methyl 2-(2-nitroethenyl)-2'-biphenylcarboxylate. Its hydrogenation followed by cyclization at elevated temperature yielded 2-(2-aminoethyl) derivative V and 5,6,7,8-tetrahydrodibenz[c,e]azocin-5-one, respectively. Reduction of the lactam ring of the substituted azocinone furnished the final product, which can alternatively be obtained directly from compound V on reaction with sodium bis(2-methoxyethoxy)hydridoaluminate. Conformation of the final product was deduced from¹H  and ¹³C  NMR and UV spectral data.

Full paper in Portable Document Format: 455a667.pdf

Chemical Papers 45 (5) 667–675 (1991)