Ce(III)-catalyzed highly efficient synthesis of pyridyl benzamides from aminopyridines and nitroolefins without external oxidants

An efficient synthesis of a variety of pyridyl benzamides from 2-aminopyridines and nitroolefins is described. This rare-earth-metal-catalyzed reaction provides the corresponding products with broad substrate scope in moderate to excellent yields, in the absence of additives and external oxidants. W...

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Published inOrganic & biomolecular chemistry Vol. 16; no. 8; pp. 1247 - 1251
Main Authors Chen, Zhengwang, Wen, Xiaowei, Qian, Yiping, Liang, Pei, Liu, Botao, Ye, Min
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2018
Royal Society of Chemistry
Subjects
Additives
Carbonyls
Chemical synthesis
Chemistry
Chemistry, Organic
Oxidants
Oxidizing agents
Physical Sciences
Pyridines
Rare earth elements
Science & Technology
Substrates
ALCOHOLS
PRACTICAL SYNTHESIS
STAUDINGER LIGATION
AMIDE SYNTHESIS
AMINES
OXIDATIVE AMIDATION
REGIOSELECTIVE SYNTHESIS
HYDROGEN-PEROXIDE
ALDEHYDES
CASCADE REACTION
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Summary:An efficient synthesis of a variety of pyridyl benzamides from 2-aminopyridines and nitroolefins is described. This rare-earth-metal-catalyzed reaction provides the corresponding products with broad substrate scope in moderate to excellent yields, in the absence of additives and external oxidants. Water is used as the source of the carbonyl oxygen atom in pyridyl benzamides. Furthermore, 2-substituted oxazolo[4,5-b] pyridines are formed in good yields under the standard conditions when 2-aminopyridin3-ols are used as the substrates.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob03113k