A convenient synthetic route to 2-aryl-N-tosylazetidines and their ZnX2 (X = I, OTf) mediated regioselective nucleophilic ring opening reactions: synthesis of gamma-iodoamines and tetrahydropyrimidines

摘要

A general and convenient synthetic route to various 2-aryl-N-tosylazetidines has been described. Their ZnX2 (X = I, OTf) mediated nucleophilic ring opening with halides and [4+2] cycloaddition reactions with various nitriles have been achieved to afford gamma-iodoamines and substituted tetrahydropyrimidines, respectively, in good to excellent yields. A mechanism for the cycloaddition reaction is proposed. (c) 2006 Elsevier Ltd. All rights reserved.