An efficient synthetic route to substituted tetrahydropyrimidines by Cu(OTf)2-mediated nucleophilic ring-opening followed by the [4+2] cycloaddition of N-tosylazetidines with nitriles

Ghorai, Manas K. ; Das, Kalpataru ; Kumar, Amit (2009) An efficient synthetic route to substituted tetrahydropyrimidines by Cu(OTf)2-mediated nucleophilic ring-opening followed by the [4+2] cycloaddition of N-tosylazetidines with nitriles Tetrahedron Letters, 50 (10). pp. 1105-1109. ISSN 0040-4039

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Official URL: http://doi.org/10.1016/j.tetlet.2008.12.035

Related URL: http://dx.doi.org/10.1016/j.tetlet.2008.12.035

Abstract

A highly efficient strategy for Cu(OTf)2-mediated SN2 type nucleophilic ring-opening followed by the [4+2] cycloaddition reactions of a number of 2-aryl-N-tosylazetidines with nitriles to afford a variety of substituted tetrahydropyrimidines in excellent yields is reported. The resulting tetrahydropyrimidines could easily be transformed into synthetically important 1,3-diamines by acid-catalyzed hydrolysis. The strategy has been extended to the synthesis of enantiomerically pure tetrahydropyrimidines from enantiopure disubstituted azetidines. The reaction proceeds through an SN2 type mechanism as proposed by us earlier.

Item Type:Article
Source:Copyright of this article belongs to Elsevier B.V.
Keywords:Azetidine; [4+2] Cycloaddition; Cu(Otf)2; Sn2; Tetrahydropyrimidine; 1,3-diamine.
ID Code:117122
Deposited On:15 Apr 2021 08:01
Last Modified:15 Apr 2021 08:01

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