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Heterogeneous Gold‐Catalyzed Cascade Hydrogen‐Transfer Strategy for Selective Synthesis of Quinazolinones in Water
Author(s) -
Tang Lin,
Zhao Xianghua,
Zou Guodong,
Zhou Yuqiang,
Yang Xingkun
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500512
Subject(s) - chemistry , catalysis , tandem , combinatorial chemistry , transfer hydrogenation , substrate (aquarium) , cascade reaction , hydrogen bond , condensation , selective reduction , nitro , organic chemistry , molecule , materials science , oceanography , physics , alkyl , ruthenium , composite material , thermodynamics , geology
Efficient and selective synthesis of quinazolinones from 2‐nitrobenzonitriles and benzylic alcohols catalyzed by TiO 2 ‐supported gold nanoparticles (Au/TiO 2 ) has been developed. Various transformations, such as dehydrogenative oxidation of C−O and C−N bonds, reduction of nitro groups, condensation of aldehydes with amines, hydration of cyano groups and cyclization, can be achieved in the tandem hydrogen‐transfer reaction. This protocol presents broad substrate scope, good tolerance to air and water, excellent recycling of the catalyst and does not require any additive, oxidant or reductant, which enables straightforward, practical and environmentally benign C−N and C−O bond formation.