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

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.

Keywords:

• Amination
• aminoquinazolines
• hexamethyldisilazane
• quinazolin-4(3H)-ones

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.