Synthesis of Quinazolines via an Iron-Catalyzed Oxidative Amination of N-H Ketimines

Cheng-yi Chen*, Fengxian He, Guangrong Tang, Huiqing Yuan, Ning Li, Jinmin Wang and Roger Faessler

*Janssen R&D, Pharmaceutical Development and Manufacturing Sciences, Small Molecule API Switzerland, Cilag AG, Hochstrasse 201, 8205 Schaffhausen, Switzerland, Email: cchen117its.jnj.com

C.-y. Chen, F. He, G. Tang, H. Yuan, N. Li, J. Wang, R. Faessler, J. Org. Chem., 2018, 83, 2395-2401.

DOI: 10.1021/acs.joc.7b02943

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Abstract

An iron-catalyzed C(sp³)-H oxidation, intramolecular C-N bond formation, and aromatization enables an efficient synthesis of quinazolines from 2-alkylamino N-H ketimine derivatives, which can be prepared by addition of various organometallic reagents to 2-alkylamino benzonitriles.

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synthetic strategy

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Key Words

quinazolines, TBHP

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ID: J42-Y2018