Synthesis of Quinolinium Salts from N-Substituted Anilines, Aldehydes, Alkynes, and Acids: Theoretical Understanding of the Mechanism and Regioselectivity

Lin Chieh Cheng, Wei Chen Chen, Rajagopal Santhoshkumar, Tzu Hsuan Chao, Mu Jeng Cheng, Chien Hong Cheng

Research output: Contribution to journalArticle

Abstract

Secondary anilines were first utilized in the four-component coupling of aniline, aldehyde, alkyne, and acid to synthesize a variety of N-substituted quinolinium salts. This method was carried out under mild reaction conditions and exhibited excellent chemo- and regioselectivities. DFT calculation was performed to analyze the cyclization step, where the interaction/distortion model provided better insight into the singular selectivity of terminal/internal alkynes in reaction.

Original languageEnglish
Pages (from-to)2116-2129
Number of pages14
JournalEuropean Journal of Organic Chemistry
Volume2020
Issue number14
DOIs
Publication statusPublished - 2020 Apr 16

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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