Journal
TETRAHEDRON
Volume 69, Issue 1, Pages 212-218Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.10.042
Keywords
Trityl chloride; Multi-component condensation; 1-Amido-alkyl-2-naphthol; 1-Thioamido-alkyl-2-naphthol; 1-Carbamato-alkyl-2-naphthol; Solvent-free
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Funding
- Research Affairs Office of Bu-Ali Sina University [32-1716]
- Payame Noor University
- Center of Excellence in Development of Chemical Method (CEDCM), Hamedan, I.R. Iran
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Trityl chloride (TrCl), efficiently catalyzes the one-pot multi-component condensation of beta-naphthol with aromatic aldehydes and amides/thioamides/carbamates such as acetamide, benzamide, nicotinamide, thioacetamide, and methylcarbamate under solvent-free and neutral conditions to afford 1-amido-alkyl-2-naphthols, 1-thioamido-alkyl-2-naphthols, and 1-carbamato-alkyl-2-naphthols in high yields and very short reaction times. Mechanistically, it is interesting that trityl chloride through the in situ generation of trityl carbocation with inherent instability is efficient as a reusable homogeneous organocatalyst in neutral media. (C) 2012 Elsevier Ltd. All rights reserved.
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