Highly Selective Cyclization and Isomerization of Propargylamines to Access Functionalized Quinolines and 1-Azadienes

Developing new organic reactions with excellent atom economy and high selectivity is significant and urgent. Herein, by ingeniously regulating the reaction conditions, highly selective transformations of propargylamines have been successfully implemented. The palladium-catalyzed cyclization of propa...

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Published inMolecules (Basel, Switzerland) Vol. 28; no. 17; p. 6259
Main Authors Wu, Zheng-Guang, Zhang, Hui, Cao, Chenhui, Lu, Chaowu, Jiang, Aiwei, He, Jie, Zhao, Qin, Tang, Yanfeng
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 26.08.2023
MDPI
Subjects
Chemical bonds
Chromatography
cyclization
heterocycle
high selectivity
Isomerization
Natural products
Palladium
propargylamine
Solvents
Vacuum distillation
Japan
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ISSN1420-3049
1420-3049
DOI10.3390/molecules28176259

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Summary:Developing new organic reactions with excellent atom economy and high selectivity is significant and urgent. Herein, by ingeniously regulating the reaction conditions, highly selective transformations of propargylamines have been successfully implemented. The palladium-catalyzed cyclization of propargylamines generates a series of functionalized quinoline heterocycles, while the base-promoted isomerization of propargylamines affords diverse 1-azadienes. Both reactions have good functional group tolerance, mild conditions, excellent atom economy and high yields of up to 93%. More importantly, these quinoline heterocycles and 1-azadienes could be flexibly transformed into valuable compounds, illustrating the validity and practicability of the propargylamine-based highly selective reactions.
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These authors contributed equally to this work.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28176259