Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5272769 | Tetrahedron Letters | 2009 | 5 Pages |
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.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Manas K. Ghorai, Kalpataru Das, Amit Kumar,