Synthesis 2013; 45(23): 3245-3250
DOI: 10.1055/s-0033-1339918
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Cyanation of Quinazoline-4-tosylates for Access to 4-CN-Functionalized Quinazolines

Xu Zhao
a   Key Laboratory of Green Chemistry, Jiangxi Province and College of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
,
Yirong Zhou
b   Key Laboratory of Small Functional Organic Molecule, Ministry of Education and College of Life Science, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China   Fax: +86(791)88120396   Email: yypeng@jxnu.edu.cn   Email: yiyuanpeng@yahoo.com
,
Qin Yang
b   Key Laboratory of Small Functional Organic Molecule, Ministry of Education and College of Life Science, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China   Fax: +86(791)88120396   Email: yypeng@jxnu.edu.cn   Email: yiyuanpeng@yahoo.com
,
Yepeng Xie
a   Key Laboratory of Green Chemistry, Jiangxi Province and College of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
,
Qiuping Ding
a   Key Laboratory of Green Chemistry, Jiangxi Province and College of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
,
Zhihong Deng
a   Key Laboratory of Green Chemistry, Jiangxi Province and College of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
,
Ming Zhang
a   Key Laboratory of Green Chemistry, Jiangxi Province and College of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
,
Jingshi Xu
a   Key Laboratory of Green Chemistry, Jiangxi Province and College of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
,
Yiyuan Peng*
a   Key Laboratory of Green Chemistry, Jiangxi Province and College of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
b   Key Laboratory of Small Functional Organic Molecule, Ministry of Education and College of Life Science, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China   Fax: +86(791)88120396   Email: yypeng@jxnu.edu.cn   Email: yiyuanpeng@yahoo.com
› Author Affiliations
Further Information

Publication History

Received: 28 July 2013

Accepted after revision: 16 September 2013

Publication Date:
14 October 2013 (online)


Abstract

A highly efficient palladium-catalyzed cyanation of quinazoline-4-tosylates is disclosed. The method is successfully developed for the direct access to various 4-CN-functionalized quinazolines, which are potentially useful as biologically and pharmaceutically active compounds. The reactions were performed under mild conditions using inexpensive copper(I) cyanide as cyano source in good to excellent yields and great functional group diversities.

Supporting Information