☆ 4.7 Article

Synthesis of Terminal N-Vinylazoles from Aromatic Aldehydes, DMSO, and Azoles Based DMSO as Terminal Carbon Synthon

ADVANCED SYNTHESIS & CATALYSIS (2021)

Journal

ADVANCED SYNTHESIS & CATALYSIS

Volume 363, Issue 19, Pages 4621-4626

Publisher

WILEY-V C H VERLAG GMBH

DOI: 10.1002/adsc.202100663

Keywords

Terminal N-vinylazoles; Aromatic Aldehydes; DMSO; Azoles; C=C and C-N bonds Formation

Categories

Chemistry, Applied Chemistry, Organic

Funding

National Natural Science Foundation of China [21572049]

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Abstract

A protocol for the synthesis of terminal N-vinylazoles from aromatic aldehydes, DMSO, and azoles has been reported, with DMSO involved in the construction of the C=C bond as a terminal carbon synthon. Both aromatic aldehydes and azoles tolerated well, yielding the corresponding terminal N-vinylazoles in 52-91%. A plausible mechanism is proposed based on preliminary experiments.

A protocol for the synthesis of terminal N-vinylazoles from aromatic aldehydes, DMSO, and azoles has been reported. In this strategy, DMSO was involved in the construction of the C=C bond as a terminal carbon synthon. Both aromatic aldehydes and azoles could be well tolerated and give the corresponding terminal N-vinylazoles in 52-91% yields. Based on preliminary experiments, a plausible mechanism is proposed.

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