Issue 82, 2015

Rh(iii)-catalyzed [5+1] oxidative cycloaddition of arylguanidines with alkynes: a novel access to C4-disubstituted 1,4-dihydroquinazolin-2-amines

Abstract

A novel and mild RhIII-catalyzed [5+1] oxidative cycloaddition between arylguanidines and alkynes efficiently affords C4-disubstituted 1,4-dihydroquinazolin-2-amines. Members of this family of heterocycles, which contain the relevant cyclic guanidine units, have shown interesting pharmacological properties. The mechanism probably involves the formation of an eight-membered rhodacycle in which the imine unit of guanidine is coordinated to the Rh center. This rhodacycle would evolve to give the C-4 disubstituted 1,4-dihydroquinazolin-2-amine skeleton.

Graphical abstract: Rh(iii)-catalyzed [5+1] oxidative cycloaddition of arylguanidines with alkynes: a novel access to C4-disubstituted 1,4-dihydroquinazolin-2-amines

Supplementary files

Article information

Article type
Communication
Submitted
30 Jul 2015
Accepted
19 Aug 2015
First published
19 Aug 2015

Chem. Commun., 2015,51, 15157-15160

Author version available

Rh(III)-catalyzed [5+1] oxidative cycloaddition of arylguanidines with alkynes: a novel access to C4-disubstituted 1,4-dihydroquinazolin-2-amines

A. Cajaraville, J. Suárez, S. López, J. A. Varela and C. Saá, Chem. Commun., 2015, 51, 15157 DOI: 10.1039/C5CC06388D

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