Synthesis 2016; 48(22): 3976-3984
DOI: 10.1055/s-0035-1562504
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Cross-Coupling of 4-Tosyloxyquinazolines with Organoindium Reagents: An Efficient Route to 4-Substituted Quinazolines

Xinglin Ye
a   National Research Center for Carbohydrate Synthesis and Key Laboratory of Small Functional Organic Molecule, Ministry of Education, and Key Laboratory of Green Chemistry of Jiangxi Province, Nanchang, Jiangxi 330022, P. R. of China   Email: yypeng@jxnu.edu.cn   Email: yiyuanpeng@yahoo.com
b   Department of Chemistry and Environmental Engineering, Jiujiang University, Jiujiang, Jiangxi, 330025, P. R. of China
,
Jianjun Yuan
a   National Research Center for Carbohydrate Synthesis and Key Laboratory of Small Functional Organic Molecule, Ministry of Education, and Key Laboratory of Green Chemistry of Jiangxi Province, Nanchang, Jiangxi 330022, P. R. of China   Email: yypeng@jxnu.edu.cn   Email: yiyuanpeng@yahoo.com
,
Yirong Zhou
a   National Research Center for Carbohydrate Synthesis and Key Laboratory of Small Functional Organic Molecule, Ministry of Education, and Key Laboratory of Green Chemistry of Jiangxi Province, Nanchang, Jiangxi 330022, P. R. of China   Email: yypeng@jxnu.edu.cn   Email: yiyuanpeng@yahoo.com
,
Zhihong Deng
a   National Research Center for Carbohydrate Synthesis and Key Laboratory of Small Functional Organic Molecule, Ministry of Education, and Key Laboratory of Green Chemistry of Jiangxi Province, Nanchang, Jiangxi 330022, P. R. of China   Email: yypeng@jxnu.edu.cn   Email: yiyuanpeng@yahoo.com
,
Xuechun Mao
a   National Research Center for Carbohydrate Synthesis and Key Laboratory of Small Functional Organic Molecule, Ministry of Education, and Key Laboratory of Green Chemistry of Jiangxi Province, Nanchang, Jiangxi 330022, P. R. of China   Email: yypeng@jxnu.edu.cn   Email: yiyuanpeng@yahoo.com
,
Yiyuan Peng*
a   National Research Center for Carbohydrate Synthesis and Key Laboratory of Small Functional Organic Molecule, Ministry of Education, and Key Laboratory of Green Chemistry of Jiangxi Province, Nanchang, Jiangxi 330022, P. R. of China   Email: yypeng@jxnu.edu.cn   Email: yiyuanpeng@yahoo.com
› Author Affiliations
Further Information

Publication History

Received: 04 April 2016

Accepted after revision: 26 May 2016

Publication Date:
25 July 2016 (online)


Abstract

An efficient route to 4-substituted quinazolines by arylation or alkylation of quinazolinones under mild conditions is described. 4-Tosyloxyquinazolines were obtained through the reaction of quinazolinones and p-methylbenzenesulfonyl chloride in the presence of K2CO3. The cross-coupling reaction of 4-tosyloxyquinazolines with organoindium reagents, carried out in tetrahydrofuran, catalyzed by Pd2(dba)3/ (2-furyl)3P led to the formation of 4-functionalized quinazolines in good to excellent yields. Higher yields were obtained by the one-pot reaction of quinazolinone, p-methylbenzenesulfonyl chloride, Pd2(dba)3-/(2-furyl)3P, and organoindium reagent. These methods using organoindium compounds as coupling partners provided an efficient route to 4-(hetero)aryl/alkylquinazolines, especially 4-substituted quinazolines bearing a halogen scaffold.

Supporting Information

 
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