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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 24
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Original Articles

One-Pot Synthesis of 4-Aminoquinazolines by Hexamethyldisilazane-Mediated Reaction of Quinazolin-4(3H)-ones with Amines

, , , , , & show all
Pages 3644-3653 | Received 20 Sep 2009, Published online: 22 Aug 2011
 

Abstract

Hexamethyldisilazane-mediated reaction of quinazolin-4(3H)-ones with primary amines led to facile formation of 4-aminoquinazolines through tandem silylation and substitution in a single pot. Excellent yields of the products (83–97%) and environmental friendliness (avoiding the use of chlorination reagents) are the advantages of this method.

ACKNOWLEGMENTS

The authors are grateful to the financial support of the National Natural Science Foundation of China (NSFC, 20876149) and the Zhejiang Provincial Natural Science Foundation of China (Y4090517).

Notes

a N(Quinazolin-4(3H)-one)/N(amine)/N(HMDS)/N[(NH4)2SO4] = 1:1.4:1.4:0.1.

b Yields refer to isolated pure products.

c N(Quinazolin-4(3H)-one)/N(amine)/N(HMDS)/N[(NH4)2SO4] = 1:2:2:0.1.

d The reaction was performed in a sealed vessel.

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