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Paper | Regular issue | Vol 48, No. 5, 1998, pp.919-927
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8104
Regioselective Synthesis of Several Heterocyclic Fused Azepines Using Diisobutylaluminum Hydride

Hidetsura Cho,* Kengo Murakami, Hiroyuki Nakanishi, Hirotaka Isoshima, Kazuhide Hayakawa, and Itsuo Uchida

*Central Pharmaceutical Research Institute, Japan Tobacco Inc., 1-1, Murasaki-cho, TAkatsuki-shi, Osaka, 569-1125, Japan

Abstract

5,6,7,8-Tetrahydrothieno[3,2-b]azepine, 5,6,7,8-tetrahydro-1H-furo[3,2-b]azepine, and 1,4,5,6,7,8-hexahydropyrrolo[3,2-b]azepine were synthesized by the ring expansion reaction of heterocyclic fused cyclohexanone oximes with diisobutylaluminum hydride (DIBAH). The mechanism of the reaction was different from that of Beckmann Rearrangement.