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Communication | Special issue | Vol 74, No. 1, 2007, pp.205-210
Published online, 12th October, 2007
DOI: 10.3987/COM-07-S(W)53
Spirocyclization of an N-Acyliminium Ion with Substituted Pyridine: Synthesis of Tricyclic Spirolactams Possessing Pyridine or Pyridone Nucleus

Hideki Abe, Kei-ichi Takaya, Kazuhiro Watanabe, Sakae Aoyagi,* Chihiro Kibayashi, and Tadashi Katoh*

*Department of Synthetic Organic Chemistry, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan

Abstract

Spirocyclization of an N-acyliminium ion with pyridine activated by a 2-methoxy substituent as an aromatic π-nucleophile was developed. The reactions proceeded in the presence of Brønsted acids at a high temperature, producing tricyclic spirolactams that possess the ability to act as conformationally constrained nicotine analogues.