Facile and Efficient Oxidation of Quinazolines into Quinazolin-4(3H)-ones by Peracetic Acid

Abstract

A new approach to synthesize quinazoline-4(3H)-ones was achieved by oxidation of quinazolines using peracetic acid, which possesses some advantages of economic reagents, simplified operation, high efficiency, and environmental friendliness. Application of this method allowed us to synthesize a series of quinazolin-4(3H)-ones with different substituents at 6 and 7 positions in good to excellent yields, including the key intermediates of tyrosine kinase inhibitors such as PD153035, Erlotinib, and Gefitinib.

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GRAPHICAL ABSTRACT

Keywords:

• 4-Anilinoquinazolines
• oxidation
• peracetic acid
• quinazolin-4(3H)-ones

ACKNOWLEDGMENTS

This work was partially supported by the School of Pharmacy, Fudan University, and the Open Project Program of Key Laboratory of Smart Drug Delivery (Fudan University), Ministry of Education, China (No. SDD2012-07), and Fudan Undergraduate Research Opportunities Program (No. 12021). The authors are grateful to Chun-Jun Guo (University of Southern California) for his very helpful advice during manuscript preparation.

Notes

^a Isolated yield.