Tetrahedron letters

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

MK Ghorai, K Das, A Kumar, A Das

Index: Ghorai, Manas K.; Das, Kalpataru; Kumar, Amit; Das, Animesh Tetrahedron Letters, 2006 , vol. 47, # 30 p. 5393 - 5397

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Citation Number: 37

Abstract

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 γ-iodoamines and substituted tetrahydropyrimidines, respectively, in good to excellent yields. A mechanism for the cycloaddition reaction is proposed.