Efficient synthesis of perfluoroalkylated quinolines via a metal-free cascade Michael addition/intramolecular rearrangement cyclization process

被引：11
|
作者：
Wu, Jun [1 ,2 ]
Zhang, Hui [1 ,3 ,4 ]
Ding, Xiao [2 ]
Tan, Xuefei [2 ]
Shen, Hong C. [2 ]
Chen, Jie [1 ]
Song, Liping [1 ]
Cao, Weiguo [1 ,5 ]
机构：
[1] Shanghai Univ, Dept Chem, 99 Shangda Rd, Shanghai 200444, Peoples R China
[2] Roche R&D Ctr China Ltd, Roche Innovat Ctr Shanghai, 720 Cailun Rd, Shanghai 201203, Peoples R China
[3] Shanghai Univ, Lab Microstruct & Instrumental Anal, Shanghai 200444, Peoples R China
[4] Shanghai Univ, Res Ctr, Shanghai 200444, Peoples R China
[5] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON | 2020年 / 76卷 / 43期
基金：
中国国家自然科学基金;
关键词：
Quinoline; Metal-free; Michael addition; Perfluoroalkylated alkyne; Intramolecular rearrangement; ONE-POT SYNTHESIS; TRIFLUOROACETIMIDOYL CHLORIDES; 2-TRIFLUOROMETHYL QUINOLINES; FACILE SYNTHESIS; SKRAUP; DERIVATIVES; MECHANISM; PYRIDINE; ISATINS; KETONES;
D O I：
10.1016/j.tet.2020.131518
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-Perfluoroalkylated quinolines were efficiently synthesized via the Michael addition of perfluoroalk-2-ynoates with isatins, followed by the reaction with alcohols through an intramolecular rearrangement cyclization in the presence of Na2CO3. Under the mild and metal-free reaction conditions, a broad scope of quinolines was synthesized and the mechanism was proposed. (C) 2020 Elsevier Ltd. All rights reserved.
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页数：7
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