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Communication | Regular issue | Vol 34, No. 5, 1992, pp.881-884
Published online, 1st January, 1970
DOI: 10.3987/COM-92-5987
A Convenient, One-Pot Synthesis of Tropocoronands and Tropopodans by Use of the Heterocycle-Exchange Reaction of Benzo[b]cyclohepta[e][1,4]oxazine

Tetsuo Nozoe,* Kimio Shindo,* Hidetsugu Wakabayashi, and Sumio Ishikawa

*Department of Chemistry, Faculty of Science, Josai University, Sakado, Saitama 350-02, Japan

Abstract

Treatment of benzo[b]cyclohepta[e][1,4]oxzine (5) with 1.2 equiv. of α,ω-diaminoalkanes (2, n=4-12) in ethanol at 80 °C gave tropocoronands (4, n=4-12) in one step in high yields, while the reaction of 5 with an excess of 2 afforded tropopodands (6, n=4-6). The reactions of 5 with 2 (n=2,3) yielded bicyclic pyrazino or diazepino compounds in high yields. Coronands [14 (instead of 4a) and 4b (n=3)] were, however, obtained by the reaction of 5 with N-acetyldiaminoalkanes. The reaction of 5 with α,ω-amino alcohol afforded the corresponding podands.