Efficient Tandem Addition/Cyclization for Access to 2,4-Diarylquinazolines via Catalytic Carbopalladation of Nitriles

Julin Gong; Kun Hu; Yetong Zhang; Yinlin Shao; Tianxing Cheng; Maolin Hu; Jiuxi Chen

doi:10.3390/molecules24030463

Efficient Tandem Addition/Cyclization for Access to 2,4-Diarylquinazolines via Catalytic Carbopalladation of Nitriles

Molecules. 2019 Jan 28;24(3):463. doi: 10.3390/molecules24030463.

Authors

Julin Gong¹, Kun Hu², Yetong Zhang³, Yinlin Shao⁴, Tianxing Cheng⁵, Maolin Hu⁶, Jiuxi Chen⁷

Affiliations

¹ College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, China. 16451282199@stu.wzu.edu.cn.
² College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, China. hukun15@163.com.
³ College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, China. 16451282259@stu.wzu.edu.cn.
⁴ College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, China. shaoyl@wzu.edu.cn.
⁵ College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, China. ctx@wzu.edu.cn.
⁶ College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, China. maolin@wzu.edu.cn.
⁷ College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, China. jiuxichen@wzu.edu.cn.

Abstract

The first example of the palladium-catalyzed tandem addition/cyclization of 2-(benzylidenamino)benzonitriles with arylboronic acids has been developed. This transformation features good functional group tolerance and provides an alternative synthetic pathway to access 2,4-diarylquinazolines in moderate to good yields. A plausible mechanism for the formation of 2,4-diarylquinazolines involving sequential nucleophilic addition followed by an intramolecular cyclization is proposed.

Keywords: carbopalladation; nitrile; palladium-catalyzed; quinazoline; tandem reaction.

MeSH terms

Biochemical Phenomena
Catalysis
Cyclization
Nitriles / chemistry*
Palladium / chemistry*
Quinazolines / chemistry*

Substances

Nitriles
Quinazolines
Palladium

Abstract

MeSH terms

Substances

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