Studies on Azetidine Derivatives. I. Synthesis of 3-Substituted Azetidine Derivatives

In order to find pharmacologically active azetidine derivatives, convenient procedures for the synthesis of 3-substituted azetidines have been investigated. 3-Azetidinyl mesylates (IV), prepared by treatment of azetidin-3-ols (I) with sulfenes, were shown to be useful intermediates for the synthesis of 3-substituted azetidines, 3-amino-, 3-cyano-, 3-guanidinoazetidines (V, VI and VIII) and azetidine-3-carboxylic acids (VII) via VI. 1-Cyclohexyl-3-guanidinoazetidine showed an excellent antihypertensive activity.