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One‐Pot Mannich, Aza‐Wittig and Dehydrofluorinative Aromatization Reactions for Direct Synthesis of 2,3‐Disubstituted 4‐Aminoquinolines
Author(s) -
Zhang Xiaofeng,
Ma Xiaoming,
Qiu Weiqi,
Awad JohnMark,
Evans Jason,
Zhang Wei
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000734
Subject(s) - chemistry , aromatization , wittig reaction , aminoquinolines , combinatorial chemistry , atom economy , organic chemistry , mannich reaction , catalysis
One‐pot synthesis of 2,3‐disubstituted 4‐aminoquinolines is developed through a three‐component reaction of 2‐azidobenzaldehydes, α ‐fluoro‐ β ‐ketoesters and amines involving cascade Mannich, aza‐Wittig and dehydrofluorinative aromatization. The method is applicable to other functionalized quinolines. It is a pot, atom and step economy (PASE) synthesis of biologically interesting 4‐aminoquinolines relevant to hydroxychloroquine and chloroquine.