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Masked 3-Aminoindan-1-ones by a Palladium-Catalyzed Three-Component Annulation Reaction
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Abstract
A new palladium(0)-catalyzed three-component reaction involving a set of salicylic aldehyde triflates, ethylene glycol vinyl ether, and various secondary nucleophilic amines has been developed. Through systematic optimization experiments using multivariate design, the conditions effecting robust and convenient one-pot generation of protected 3-aminoindan-1-ones were identified. A reaction route involving an initial internal Heck arylation of the hydroxyalkyl vinyl ether, iminium ion formation, and subsequent tandem cyclization is invoked to explain the selective formation of the isolated tertiary 3-aminoindan acetals. Hydrogenolysis of orthogonally blocked 3-aminoindan-1-ones delivered primary or secondary amines after 10−20 min of microwave heating.
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This article has been cited by 12 ACS Journal articles (5 most recent appear below).
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Jiwu Ruan, Jonathan A. Iggo, and Jianliang XiaoOrganic Letters2011 13 (2), 268-271A wide range of multisubstituted 1-indanones of potential pharmaceutical use were synthesized in a one-pot fashion in moderate to excellent yields via palladium catalysis in ethylene glycol. The Heck reaction first installs an enol functionality on the ...
Hydrogen-Bonding-Promoted Oxidative Addition and Regioselective Arylation of Olefins with Aryl Chlorides
Jiwu Ruan, Jonathan A. Iggo, Neil G. Berry, and Jianliang XiaoJournal of the American Chemical Society2010 132 (46), 16689-16699Hydrogen-Bonding-Promoted Oxidative Addition and Regioselective Arylation of Olefins with Aryl Chlorides
Jiwu Ruan, Jonathan A. Iggo, Neil G. Berry, and Jianliang XiaoJournal of the American Chemical Society2010 132 (46), 16689-16699The first, general, and highly efficient catalytic system that allows a wide range of activated and unactivated aryl chlorides to couple regioselectively with olefins has been developed. The Heck arylation reaction is likely to be controlled by the ...
Highly Chemoselective Pd−C Catalytic Hydrodechlorination Leading to the Highly Efficient N-Debenzylation of Benzylamines
Chuanjie Cheng, Jianwei Sun, Lixin Xing, Jimin Xu, Xinyan Wang and Yuefei HuThe Journal of Organic Chemistry2009 74 (15), 5671-5674Highly Chemoselective Pd−C Catalytic Hydrodechlorination Leading to the Highly Efficient N-Debenzylation of Benzylamines
Chuanjie Cheng, Jianwei Sun, Lixin Xing, Jimin Xu, Xinyan Wang and Yuefei HuThe Journal of Organic Chemistry2009 74 (15), 5671-5674In the presence of 1,1,2-trichloroethane, a novel procedure for the Pd−C catalytic N-debenzylation of benzylamines was established. The method proceeded in a synergistic catalytic system and directly gave the products as crystal amine hydrochlorides in ...
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History
- Published In Issue February 04, 2005
- Received October 14, 2004
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