Potassium Iodide-Promoted One-Pot Synthesis of Fluoroalkylated Quinoxalines via a Tandem Michael Addition/Azidation/Cycloamination Approach

Fluoroalkylated quinoxlines with various groups were efficiently synthesized via a one-pot tandem Michael addition/azidation/cycloamination process. Under the mild and metal-free conditions, a bis-imine intermediate (4a) was detected and isolated for the first time. KI played a crucial role in this...

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Published inJournal of organic chemistry Vol. 83; no. 16; pp. 9422 - 9429
Main Authors Wu, Jun, Zhang, Hui, Ding, Xiao, Tan, Xuefei, Chen, Jie, He, Weimin, Deng, Hongmei, Song, Liping, Shen, Hong C, Cao, Weiguo
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.08.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
AZIDES
HETEROCYCLES
BONDS
MONO
FLUORINATION
C(SP)-H
DERIVATIVES
PERFLUOROALKYLATION
C-H AMINATION
TRIFLUOROMETHYLATION
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Summary:Fluoroalkylated quinoxlines with various groups were efficiently synthesized via a one-pot tandem Michael addition/azidation/cycloamination process. Under the mild and metal-free conditions, a bis-imine intermediate (4a) was detected and isolated for the first time. KI played a crucial role in this reaction. The mechanism was described.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b01030