- Palladium-Catalyzed Cross-Coupling of 4-Tosyloxyquinazolines with Organoindium Reagents: An Efficient Route to 4-Substituted Quinazolines
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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.
- Ye, Xinglin,Yuan, Jianjun,Zhou, Yirong,Deng, Zhihong,Mao, Xuechun,Peng, Yiyuan
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p. 3976 - 3984
(2016/11/11)
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- Synthesis of 4-arylquinazolines by arylation of quinazolin-4-ones under mild conditions
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An efficient route to 4-arylquinazolines via arylation of quinazolin-4-ones under mild condition is described. The reaction is carried out by the palladium-catalyzed coupling of quinazolin-4-ones with arylboronic acids in the presence of TsCl leading to 4-arylquinazolines in good to excellent yields. Georg Thieme Verlag Stuttgart New York.
- Qiu, Guanyinsheng,Huang, Ping,Yang, Qin,Lu, Hui,Xu, Jingshi,Deng, Zhihong,Zhang, Ming,Peng, Yiyuan
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supporting information
p. 3131 - 3136
(2013/12/04)
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