Unexpected Copper-Catalyzed Cascade Synthesis of Quinazoline Derivatives

The first example of a copper-catalyzed cascade reaction of (2-aminophenyl)methanols with aldehydes using the combination of cerium nitrate hexahydrate and ammonium chloride has been developed, leading to a wide range of 2-substituted quinazolines in moderate to excellent yields. The efficiency of t...

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Published inJournal of organic chemistry Vol. 78; no. 22; pp. 11342 - 11348
Main Authors Chen, Zhongyan, Chen, Jiuxi, Liu, Miaochang, Ding, Jinchang, Gao, Wenxia, Huang, Xiaobo, Wu, Huayue
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.11.2013
Amer Chemical Soc
Subjects
aldehydes
ammonium chloride
Catalysis
cerium
chemical reactions
Chemistry
Chemistry, Organic
Copper - chemistry
moieties
Molecular Structure
nitrates
organic chemistry
Physical Sciences
Quinazolines - chemical synthesis
Quinazolines - chemistry
Science & Technology
SYSTEM
LAPATINIB
NITROARENES
DESIGN
2-SUBSTITUTED QUINAZOLINES
BIOLOGICAL EVALUATION
RECEPTOR
INHIBITORS
DISCOVERY
WATER
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Summary:The first example of a copper-catalyzed cascade reaction of (2-aminophenyl)methanols with aldehydes using the combination of cerium nitrate hexahydrate and ammonium chloride has been developed, leading to a wide range of 2-substituted quinazolines in moderate to excellent yields. The efficiency of this transformation was demonstrated by compatibility with a wide range of functional groups. Thus, the method represents a convenient and practical strategy for synthesis of 2-substituted quinazoline derivatives.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/jo401908g