Synthesis of Quinazolin-4(3H)-ones via Pd(II)-Catalyzed Intramolecular C(sp2)–H Carboxamidation of N-arylamidines

An efficient synthesis of quinazolin-4(3H)-ones from N-arylamidines, through palladium-catalyzed intramolecular C(sp2)–H carboxamidation, has been developed. The reaction, carried out in the presence of 1.0 equiv of CuO as oxidant under atmospheric pressure of CO, provides diversified 2-aryl(alkyl)q...

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Bibliographic Details
Published in:Journal of organic chemistry 2011-08, Vol.76 (15), p.6362-6366
Main Authors: Ma, Bin, Wang, Yong, Peng, Jiangling, Zhu, Qiang
Format: Article
Language:English
Subjects:
Amidines - chemistry
Aniline Compounds - chemistry
Catalysis
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Magnetic Resonance Spectroscopy
Molecular Structure
Nitriles - chemistry
Noncondensed benzenic compounds
Organic chemistry
Palladium - chemistry
Preparations and properties
Quinazolinones - chemical synthesis
Quinazolinones - chemistry
Stereoisomerism
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Summary:An efficient synthesis of quinazolin-4(3H)-ones from N-arylamidines, through palladium-catalyzed intramolecular C(sp2)–H carboxamidation, has been developed. The reaction, carried out in the presence of 1.0 equiv of CuO as oxidant under atmospheric pressure of CO, provides diversified 2-aryl(alkyl)quinazolin-4(3H)-ones in reasonable to good yields from N-arylamidines, which are readily derived from anilines and nitriles. Compared with existing approaches to quinazolin-4(3H)-ones, the current strategy features atom-economy and step-efficiency.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo2007362