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

Chemical Communications : Chem Comm
Ana CajaravilleC Saa

Abstract

A novel and mild Rh(III)-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.

References

Oct 20, 2005·Journal of the American Chemical Society·W C Peter TsangStephen L Buchwald
Nov 10, 2006·Chemical Reviews·Gilson Zeni, Richard C Larock
Jan 30, 2008·Angewandte Chemie·Gordon Brasche, Stephen L Buchwald
Jun 26, 2009·Journal of the American Chemical Society·David R StuartKeith Fagnou
Jul 18, 2009·Journal of the American Chemical Society·Tian-Sheng MeiJin-Quan Yu
Aug 27, 2009·Journal of the American Chemical Society·Nicolas Guimond, Keith Fagnou
Jul 29, 2010·Journal of the American Chemical Society·Todd K Hyster, Tomislav Rovis
Dec 8, 2010·Journal of the American Chemical Society·David R StuartKeith Fagnou
May 26, 2011·Angewandte Chemie·Lutz AckermannNora Hofmann
Dec 14, 2011·Accounts of Chemical Research·Denise A ColbyJonathan A Ellman
Dec 15, 2011·Accounts of Chemical Research·Keary M EngleJin-Quan Yu
Feb 16, 2012·Chemical Communications : Chem Comm·Hongban ZhongJianhui Huang
Sep 1, 2012·Chemical Reviews·Percia Beatrice ArockiamPierre H Dixneuf
Sep 22, 2012·Angewandte Chemie·Nadine KuhlFrank Glorius
Sep 27, 2012·Chemical Communications : Chem Comm·Wang ZhouGuo-Jun Deng
Nov 14, 2013·Journal of the American Chemical Society·Rong ZengShengming Ma
Dec 18, 2013·Chemical Society Reviews·Yoshihiko Yamamoto
May 13, 2014·Organic Letters·Kazutaka TakamatsuMasahiro Miura
Dec 23, 2014·Chemical Reviews·Xun-Xiang GuoWanbin Zhang

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