N-Heterocyclic carbene-catalyzed [3 + 3] annulation of bromoenals with 2-aminochromones to access chromeno[2,3-]pyridinones

N-Heterocyclic carbene-catalyzed [3 + 3] annulation of bromoenals with 2-aminochromones has been successfully developed. A structurally diverse set of chromeno[2,3- b ]pyridinones was efficiently constructed in acceptable to excellent yields. The reaction features mild reaction conditions, a broad s...

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Published inOrganic & biomolecular chemistry Vol. 19; no. 22; pp. 4882 - 4886
Main Authors Jiang, Pengrui, Guo, Jingcheng, Gong, Minghua, Zhou, Xiangui, Cao, Wei, Fu, Zhenqian, Huang, Wei
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 09.06.2021
Royal Society of Chemistry
Subjects
Chemical reactions
Chemistry
Chemistry, Organic
Construction standards
Crystallography
Organic chemistry
Physical Sciences
Science & Technology
Substrates
HIGHLY ENANTIOSELECTIVE SYNTHESIS
CHROMONE
CYCLOADDITION
DIHYDROPYRIDINONES
ESTERS
AEROBIC OXIDATION
NHC-CATALYSIS
ORGANOCATALYTIC ACTIVATION
ENALS
CYCLOCONDENSATION
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Summary:N-Heterocyclic carbene-catalyzed [3 + 3] annulation of bromoenals with 2-aminochromones has been successfully developed. A structurally diverse set of chromeno[2,3- b ]pyridinones was efficiently constructed in acceptable to excellent yields. The reaction features mild reaction conditions, a broad substrate scope, and easy scale-up. 2-Aminochromones were found as novel enamines used in N-heterocyclic carbene-catalyzed [3 + 3] annulation, delivering a structurally diverse set of chromeno[2,3- b ]pyridinones.
Bibliography:Electronic supplementary information (ESI) available. CCDC
For ESI and crystallographic data in CIF or other electronic format see DOI
10.1039/d1ob00720c
2081889
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob00720c