HETEROCYCLES

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■ Versatile Methods of Synthesis of 5 to 8-Membered Ring N-Heterocycles via Intramolectlar Cycloadditons of Allylamines

K. M. Lokanatha Rai and Alfred Hassner*

*Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel

Abstract

N-Tosylallylamines or homoallylamines were monoalkylated with dibromoalkanes to produce bromoalkylamines 3 or 7. The latter were converted to unsaturated nitro derivatives which, via nitrile oxides, underwent intramolecular cycloaddition of the bromo derivatives 3 either via azides to fused triazolines or by free radical reaction to pyrrolidines is also described. These reactions provide an entry into functionalized 5 to 8 membered ring heterocycles.