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Synthesis of Quinolinium Salts from N ‐Substituted Anilines, Aldehydes, Alkynes, and Acids: Theoretical Understanding of the Mechanism and Regioselectivity
Author(s) -
Cheng LinChieh,
Chen WeiChen,
Santhoshkumar Rajagopal,
Chao TzuHsuan,
Cheng MuJeng,
Cheng ChienHong
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000178
Subject(s) - chemistry , regioselectivity , alkyne , aldehyde , aniline , selectivity , combinatorial chemistry , reaction mechanism , organic chemistry , catalysis
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.