Synthesis of 2-substituted quinazolines by CsOH-mediated direct aerobic oxidative cyclocondensation of 2-aminoarylmethanols with nitriles in air

Green Chem., 2017, Advance Article
DOI: 10.1039/C7GC00977A, Communication

Song Yao, Kaijing Zhou, Jiabing Wang, Hongen Cao, Lei Yu, Jianzhang Wu, Peihong Qiu, Qing Xu
An atom-efficient synthesis of 2-substituted quinazolines is developed by a CsOH-mediated aerobic oxidative reaction of 2-aminoarylmethanols and nitriles in air.

Synthesis of 2-substituted quinazolines by CsOH-mediated direct aerobic oxidative cyclocondensation of 2-aminoarylmethanols with nitriles in air

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• From the journal:

  Green Chemistry

Synthesis of 2-substituted quinazolines by CsOH-mediated direct aerobic oxidative cyclocondensation of 2-aminoarylmethanols with nitriles in air

Song Yao,ab  Kaijing Zhou,b  Jiabing Wang,a  Hongen Cao,c  Lei Yu,c  Jianzhang Wu,*a  Peihong Qiu*a  and  Qing Xu*abc 

 Author affiliations

*Corresponding authors

aChemical Biology Research Center, College of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou, China
E-mail: wjzwzmu@163.com, wzqph@163.com
Tel: +86-158-25672558

bCollege of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, P. R. China
E-mail: qing-xu@wzu.edu.cn
Fax: +86-577-86689302
Tel: +86-138-57745327

cInstitute of Pesticide, School of Horticulture and Plant Protection and School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, China

Abstract

By using air as the superior oxidant, a highly atom-efficient synthesis of 2-substituted quinazolines is developed by a CsOH-mediated direct aerobic oxidative reaction of the readily available and stable 2-aminoarylmethanols and nitriles. Effectively working as the promoter in the alcohol oxidation, nitrile hydration, and cyclocondensation steps, CsOH is the best base for the reaction. A similar method can also be extended to the synthesis of substituted quinolines starting from methyl ketones instead of nitriles.

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