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 |
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| Authors: | Manas K Ghorai Kalpataru Das Amit Kumar Animesh Das |
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| Institution: | Department of Chemistry, Indian Institute of Technology, Kanpur 208 016, India |
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| 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. |
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| Keywords: | 2-Aryl-N-tosylazetidine [4+2] Cycloaddition ZnX2 (X = I OTf) γ-Iodoamines Tetrahydropyrimidine |
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