Transition-Metal-Free Synthesis of Indolizines from Electron-Deficient Alkenes via One-Pot Reaction Using TEMPO as an Oxidant

A one-pot method for the synthesis of multisubstituted indolizines from alpha-halo carbonyl compounds, pyridines, and electron-deficient alkenes is reported. The oxidative dehydrogenation reaction takes place under transition-metal-free conditions using TEMPO as an oxidant. This protocol uses ready...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 48; no. 3; pp. 413 - 420
Main Authors Shi, Fei, Zhang, Yu, Lu, Zhaole, Zhu, Xiaolei, Kan, Weiqiu, Wang, Xiang, Hu, Huayou
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 02.02.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
tandem reaction
alkenes
BOND-CLEAVAGE
ALCOHOLS
N-ylide
FLUORESCENCE
C-C
AEROBIC OXIDATION
dehydrogenation
CARBON-CARBON
INHIBITORS
DERIVATIVES
1,3-dipolar cycloaddition
MOLECULAR-OXYGEN
EQUIVALENT
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Summary:A one-pot method for the synthesis of multisubstituted indolizines from alpha-halo carbonyl compounds, pyridines, and electron-deficient alkenes is reported. The oxidative dehydrogenation reaction takes place under transition-metal-free conditions using TEMPO as an oxidant. This protocol uses ready available starting materials in a convenient procedure under mild reaction conditions.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0035-1560973