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One-Pot Synthesis of 2-Substituted Indoles from 2-Aminobenzyl Phosphonium Salts. A Formal Total Synthesis of Arcyriacyanin A
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Abstract
The reaction of (2-aminobenzyl) triphenylphosphonium bromide with aromatic aldehydes or α,β-unsaturated aldehydes under microwave-assisted conditions constitutes a new synthesis of 2-substituted indoles in high yields (81−97%) in a one-pot reaction. The adduct from indole-4-carboxaldehyde was an advanced intermediate in the synthesis of arcyriacyanin A.
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This article has been cited by 5 ACS Journal articles (5 most recent appear below).
Iodine-Induced Regioselective C−C and C−N Bonds Formation of N-Protected Indoles
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Synthesis of Substituted Indole from 2-Aminobenzaldehyde through [1,2]-Aryl Shift
Patrick Levesque and Pierre-André FournierThe Journal of Organic Chemistry2010 75 (20), 7033-7036Synthesis of Substituted Indole from 2-Aminobenzaldehyde through [1,2]-Aryl Shift
Patrick Levesque and Pierre-André FournierThe Journal of Organic Chemistry2010 75 (20), 7033-7036A mild, efficient, and simple method for the synthesis of 3-ethoxycarbonylindoles has been developed. Addition of ethyl diazoacetate (EDA) to 2-aminobenzaldehydes cleanly affords the indole core. As opposed to other common approaches for the synthesis of ...
Comprehensive Survey of Chemical Libraries for Drug Discovery and Chemical Biology: 2008
Roland E. Dolle, Bertrand Le Bourdonnec, Allan J. Goodman, Guillermo A. Morales, Craig J. Thomas and Wei ZhangJournal of Combinatorial Chemistry2009 11 (5), 739-790Comprehensive Survey of Chemical Libraries for Drug Discovery and Chemical Biology: 2008
Roland E. Dolle, Bertrand Le Bourdonnec, Allan J. Goodman, Guillermo A. Morales, Craig J. Thomas and Wei ZhangJournal of Combinatorial Chemistry2009 11 (5), 739-790
A Flexible Synthesis of 2,3-Disubstituted Indoles from Aminobenzyl Phosphonium Salts. A Direct Synthesis of Rutaecarpine
George A. Kraus and Haitao GuoThe Journal of Organic Chemistry2009 74 (15), 5337-5341A Flexible Synthesis of 2,3-Disubstituted Indoles from Aminobenzyl Phosphonium Salts. A Direct Synthesis of Rutaecarpine
George A. Kraus and Haitao GuoThe Journal of Organic Chemistry2009 74 (15), 5337-5341The reaction of substituted (2-aminobenzyl)triphenylphosphonium bromides with aromatic aldehydes or α,β-unsaturated aldehydes constitutes a new synthesis of 2,3-disubstitued indoles in high yields. The adduct from 4-oxo-3,4-dihydroquinazoline-2-...
Modular Synthesis of Indoles from Imines and o-Dihaloarenes or o-Chlorosulfonates by a Pd-Catalyzed Cascade Process
José Barluenga, Agustín Jiménez-Aquino, Fernando Aznar and Carlos ValdésJournal of the American Chemical Society2009 131 (11), 4031-4041Modular Synthesis of Indoles from Imines and o-Dihaloarenes or o-Chlorosulfonates by a Pd-Catalyzed Cascade Process
José Barluenga, Agustín Jiménez-Aquino, Fernando Aznar and Carlos ValdésJournal of the American Chemical Society2009 131 (11), 4031-4041A detailed study of the scope of a new Pd-catalyzed synthesis of indoles from 1,2-dihaloarenes and o-halobenzene sulfonates and imines is described. The cascade reaction comprises an imine α-arylation followed by an intramolecular C−N bond-forming ...
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History
- Published In Issue July 17, 2008
- Article ASAPJune 24, 2008
- Received: May 05, 2008
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