Unexpected straightforward formation of trifluoromethylated pyrido [2,3-d]pyrimidine derivatives via one-pot, MCRs

被引：10
作者：
Wang, Yang [1 ]
Zhou, Lu [1 ]
Zhu, Yingjun [1 ]
Zhang, Min [1 ]
Song, Liping [1 ,2 ]
Deng, Hongmei [3 ]
机构：
[1] Shanghai Univ, Sch Sci, Dept Chem, 99 Shangda Rd, Shanghai 200444, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 354 Fenglin Rd, Shanghai 200032, Peoples R China
[3] Shanghai Univ, Lab Microstruct, Shanghai, Peoples R China
来源：
JOURNAL OF FLUORINE CHEMISTRY | 2017年 / 200卷
基金：
中国国家自然科学基金;
关键词：
Fluorinated heterocycles; Michael addition; Pyridopyrimidine; Multi-component reactions; MULTICOMPONENT REACTIONS; 3-COMPONENT SYNTHESIS; KINASE INHIBITORS; DIURETIC ACTIVITY; IN-VITRO; CATALYST; WATER; PYRIDOPYRIMIDINE; NANOPARTICLES; CHEMISTRY;
D O I：
10.1016/j.jfluchem.2017.06.016
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
An efficient synthesis of trifluoromethylated pyrido[2,3-d]pyrimidine derivatives was achieved via tandem Knoevenagel- Michael addition of 6-aminopyrimidine-2,4(1H,3H)-diotie (1), aryldehyde (2) and ethyl 4,4,4-trifluoro-3-oxobutanoate (3) in refluxed DMSO in the presence of 25 mol% of piperidine as a catalyst. Compared with the stability of alpha-trifluoromethylated hemi-aminal or himi-ketal moiety, this protocol straightforwardly afforded the unexpected aromatized compounds via a spontaneous dehydration, followed by an auto-oxidation under the present reaction conditions. The structures of new compounds were determined by spectroscopic methods In addition, a possible mechanism for the formation of compound 4 was presented.
引用
收藏
页码：162 / 168
页数：7
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