Synthesis of Nitrogen-containing Heterocyclic Compounds through Nitrilium Salt. I. Reaction of Nitriles with 2-(α-Hydroxymethyl, -ethyl, and -isopropyl) cyclohexanol in the Presence of Acid

Abstract

Several kinds of bicyclic nitrogen-containing heterocycles were synthesized by the Ritter reaction of 1, 3-glycols (IX, X, and XI) and acetonitrile. Three types of compounds, hexahydrobenzoxazoles (XII and XVIII), hexahydro-3H-indoles (XIII, XIX, and XXXII), and hexahydrobenzoxazines (XXX and XXXI), were obtained. XII and XIII were obtained from IX, XVIII and XIX from X, and XXX, XXXI, and XXXII from XI. XIX underwent facile autoxidation to form a 3-hydroxy compound (XXIII).