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One‐pot Synthesis of Aromatic Fused 2,3‐Dihydroindanone by Tandem Pauson‐Khand/Michael/Henry Reaction
Author(s) -
Li Mingming,
Xing Ping,
Huang Zuogang,
Jiang Biao
Publication year - 2013
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201201118
Subject(s) - chemistry , nitromethane , cyclopentenone , michael reaction , cascade reaction , intermolecular force , tandem , pauson–khand reaction , isoindoline , one pot synthesis , organic chemistry , nitroaldol reaction , combinatorial chemistry , catalysis , molecule , enantioselective synthesis , materials science , composite material
The intermolecular Pauson‐Khand reaction between 2‐ethynylbenzaldehyde and ethylene promoted by dimethyl sulfide can be utilized to synthesize 2‐(2‐formylphenyl)cyclopentenone efficiently. This compound and its derivatives undergo a cascade process of Michael addition reaction followed by Henry reaction with nitromethane to construct substituted aromatic fused 2,3‐dihydroindanones. Furthermore, direct one‐pot synthesis of aromatic fused 2,3‐dihydroindanones from 2‐ethynylbenzaldehyde is achieved.