Ultrasound-Assisted Rapid Synthesis of Functionalized 1,2-Teraryls by Ring Transformation Methodology

Abstract

The function of styryl acetate as a carbanion nucleophile source has been explored in the ring transformation reaction of 2H-pyranones. The ultrasound-assisted carbanion-induced ring transformation of 4-amino-6-aryl-3-cyano-2H-pyran-2-ones using (E)-styryl acetate in the presence of KOH and DMF at room temperature is presented as an alternative strategy for the synthesis of functionalized 1,2-teraryls in high yields. This metal-free methodology provides easy access to a series of 1,2-teraryls and features broad functional group tolerance and mild reaction condition. Single crystal X-ray diffraction analysis of 4-(piperidin-1-yl)-6-(thiophen-2-yl)-[1,1′-biphenyl]-3-carbonitrile indicated that the crystal belongs to monoclinic system with a P21 space group having twisted aryl rings.

Key words

1,2-teraryls - ring transformation methodology - 2H-pyranones - ultrasound-assisted synthesis - terphenyls - metal-free reaction - carbanion-induced reaction

Publication History

Received: 03 May 2022

Accepted after revision: 18 May 2022

Accepted Manuscript online:
18 May 2022

Article published online:
09 August 2022

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