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Note | Regular issue | Vol 55, No. 8, 2001, pp.1519-1526
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9240
Synthesis of Tetracyclic Dibenzo[c,f]azepine and Benzo[f]thieno[3,2-c]azepine Derivatives via N-Acyliminium Ion Cyclization

Jae Yeol Lee,* Nam Jun Baek, Sook Ja Lee, Hokoon Park, and Yong Sup Lee

*Division of Life Sciences, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 131-650, Korea

Abstract

Tetracyclic dibenzo[c,f]-4-oxopyrrolo[1,2-c]azepine (2a), dibenzo[c,f]-5-oxopiperido[1,2-c]azepine (2b), benzo[f]-4-oxopyrrolo[1,2-a]thieno[3,2-c]azepine (2c), and benzo[f]-5-oxopiperido[1,2-a]thieno[3,2-c]azepine (2d) were prepared through intramolecular N-acyliminium ion cyclization of hydroxylactams (3a-d) with aromatic or heteroaromatic rings such as benzene and thiophene as a p-nucleophile. In the case of furan ring, the hydroxylactams (3e, f) were completely decomposed under the acidic conditions (formic acid or methanesulfonic acid). Subsequent reduction of 2a-d with BF3·O(C2H5)2 and BH3·S(CH3)2 finally provided the tetracyclic dibenzo[c,f]pyrrolo[1,2-c]azepine (1a), dibenzo[c,f]piperido[1,2-c]azepine (1b), benzo[f]pyrrolo[1,2-a]thieno[3,2-c]azepine (1c), and benzo[f]piperido[1,2-a]thieno[3,2-c]azepine derivatives (1d) as analogues of mianserin.