Rh(III)‐Catalyzed [5+1] Oxidative Cycloaddition of Arylguanidines with Alkynes: A Novel Access to C4‐Disubstituted 1,4‐ Dihydroquinazolin‐2‐amines

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Chem. Commun. 2015, 51, 15157-15160.pdf (377.97 KB)
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URI: http://hdl.handle.net/10347/23348
ISSN: 1359-7345
E-ISSN: 1364-548X
DOI: 10.1039/C5CC06388D

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2015

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Royal Society of Chemistry
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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.

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NOTICE: This is the peer reviewed version of the following article: Cajaraville, A., Suárez, J., López, S., Varela. J. A., Saá, C. (2015). Rh(III)‐Catalyzed [5+1] Oxidative Cycloaddition of Arylguanidines with Alkynes: A Novel Access to C4‐Disubstituted 1,4‐ Dihydroquinazolin‐2‐amines. Chem. Commun., 51, 82, 15157-15160. [doi: 10.1039/C5CC06388D]. This article may be used for non-commercial purposes in accordance with The Royal Society of Chemistry Terms and Conditions for self-archiving

Keywords

Alkynes| Arylguanidines| Cyclization| Dihydroquinazolinamines| Rhodium

Bibliographic citation

Cajaraville, A., Suárez, J., López, S., Varela. J. A., Saá, C. (2015). Rh(III)‐Catalyzed [5+1] Oxidative Cycloaddition of Arylguanidines with Alkynes: A Novel Access to C4‐Disubstituted 1,4‐ Dihydroquinazolin‐2‐amines. Chem. Commun., 51, 82, 15157-15160

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This work was supported by MICINN (project CTQ2011‐28258), Xunta de Galicia and European Regional Development Fund (projects GRC2014/032 and EM 2012/051). A. C. and J. S. thank Spanish MICINN and Xunta de Galicia for a predoctoral FPI fellowship and postdoctoral contract, respectively

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© The Royal Society of Chemistry 2015. This article may be used for non-commercial purposes in accordance with The Royal Society of Chemistry Terms and Conditions for self-archiving

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