期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2011, 期 20-21, 页码 3695-3699出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100426
关键词
Sulfur; Aldehydes; Imine precursors; Multicomponent reactions; Alkylation
资金
- Centre National de la Recherche Scientifique (CNRS)
- L'Institut de Chimie des Substances Naturelles (ICSN)
A novel one-pot, three-component synthesis of N-acyl or N-carbamoyl-alpha-amidosulfides 4 is described. The three-component reaction of aldehydes 1, primary carbamates (or amides) 2 and phenylsulfinic acid (6a) afforded alpha-amidosulfones 7, which after addition of sodium thiolate were in situ transformed into stable alpha-amidosulfides 4 in good to excellent yields. We demonstrated that silver salts or Bronsted acids were able to promote the formation of aliphatic and aromatic N-acylimines from 4 in quantitative yield under mild conditions. The phosphoric acid catalyzed Friedel-Crafts alkylation of 3-substituted indoles with alpha-amidosulfides 4 leading to 2,3-disubstitued indoles was also documented.
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