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Paper | Regular issue | Vol 36, No. 5, 1993, pp.1065-1074
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6276
Synthesis of 6,7-Dihydro-8-(4-methyl-1-piperazinyl)-[1]benzoxepino[4,5-c]quinoline as Potential 5-HT3 Receptor Ligand

Maurizio Anzini,* Andrea Cappelli, and Salvatore Vomero

*Dipartimento Farmaco Chimico Technlogico, Università degli Studi di Siena, Banchi di Sotto, 55 - 53100 Siena, Italy

Abstract

Two synthetic routes to the achievement of the title compound are described. The [1]benzoxepino[4,5-c]quinoline nucleus was prepared by nucleophilic aromatic fluoride displacement-cyclization and functionalized with N-methylpiperazine moiety. Alternatively the oxepino ring closure is shifted as the final step. An oxepine ring cleavage occurred in compounds (9) and (3); a mechanistical interpretation is proposed.