Selective synthesis of eight-membered cyclic ureas by the [6 + 2] cycloaddition reaction of 2-vinylazetidines and electron-deficient isocyanates

Abstract

The [6 + 2] cycloaddition reaction of 2-vinylazetidines with electron-deficient isocyanates such as tosyl isocyanate proceeded smoothly in the absence of the catalyst at room temperature, and various cyclic ureas were isolated in good to high yields. Electron-deficient allenes also reacted with the 2-vinylazetidine, and the corresponding azocine derivatives were isolated.