Divergent synthesis of nitrogen heterocycles via H2O-mediated hydride transfer reactions

The H2O-promoted controllable synthesis of diverse nitrogen heterocycles from readily available feedstocks was developed by a hydride transfer strategy. A variety of 3-carboxyl and 3-acyl substituted tetrahydroquinolines and 3,4-dihydroquinolin-2(1H)-ones were obtained via cascade Knoevenagel conden...

Full description

Saved in:
Bibliographic Details
Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 25; no. 13; pp. 5134 - 5141
Main Authors Hu, Fangzhi, Sun, Zhipeng, Pan, Mengzhe, Wang, Liang, Xu, Lubin, Liu, Xiong-Li, Li, Shuai-Shuai
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 03.07.2023
Royal Society of Chemistry
Subjects
Acylation
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Controllability
Dealkylation
Decarboxylation
Green & Sustainable Science & Technology
Green chemistry
Hydrides
Nitrogen
Physical Sciences
Science & Technology
Science & Technology - Other Topics
OXIDATION
PALLADIUM
DIASTEREOSELECTIVE SYNTHESIS
CONSTRUCTION
TETRAHYDROQUINOLINE
INHIBITORS
C-H FUNCTIONALIZATION
BOND
CYCLIZATION
C(SP)-H FUNCTIONALIZATION
Online AccessGet full text

Cover

More Information
Summary:The H2O-promoted controllable synthesis of diverse nitrogen heterocycles from readily available feedstocks was developed by a hydride transfer strategy. A variety of 3-carboxyl and 3-acyl substituted tetrahydroquinolines and 3,4-dihydroquinolin-2(1H)-ones were obtained via cascade Knoevenagel condensation/[1,5]-hydride transfer/cyclization/hydrolysis/decarboxylation and cascade Knoevenagel condensation/[1,5]-hydride transfer/N-dealkylation/N-acylation processes, respectively. In addition, the synthetic utility of the methodology and mechanistic studies were also well presented.
ISSN:1463-9262
1463-9270
DOI:10.1039/d3gc00166k