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

Ghorai, Manas K. ; Das, Kalpataru ; Kumar, Amit ; Das, Animesh (2006) A convenient synthetic route to 2-aryl-N-tosylazetidines and their ZnX2 (X=I, OTf) mediated regioselective nucleophilic ring opening reactions: synthesis of γ-iodoamines and tetrahydropyrimidines Tetrahedron Letters, 47 (30). pp. 5393-5397. ISSN 0040-4039

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Official URL: http://doi.org/10.1016/j.tetlet.2006.05.058

Related URL: http://dx.doi.org/10.1016/j.tetlet.2006.05.058

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.

Item Type:Article
Source:Copyright of this article belongs to Elsevier B.V.
Keywords:2-Aryl-N-tosylazetidine; [4+2] Cycloaddition; ZnX2 (X = I, OTf); γ-Iodoamines; Tetrahydropyrimidine.
ID Code:117135
Deposited On:15 Apr 2021 08:10
Last Modified:15 Apr 2021 08:10

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