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DOI: 10.1055/s-0029-1219917
An Efficient One-Pot Synthesis of Substituted 2-Aminothiophenes via Three-Component Gewald Reaction Catalyzed by l-Proline
Publication History
Publication Date:
06 May 2010 (online)
Abstract
An efficient one-pot procedure for the direct catalytic synthesis of substituted 2-aminothiophenes catalyzed by l-proline under mild reaction conditions has been developed. A variety of functionalized 2-aminothiophene scaffolds were assembled in high yields by this catalytic protocol. Low catalyst loading, simple procedure, and high yields are the important attributes of this methodology.
Key words
Gewald reaction - 2-aminothiophene - one-pot - multicomponent - Knoevenagel reaction
- Supporting Information for this article is available online:
- Supporting Information
- Primary data for this article are available online and can be cited using the following DOI: 10.4125/pd0002th:
- Primary Data MS data and associated files for the ¹H and ¹³C NMR spectra for the compounds 3a-o are summarized.
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References and Notes
General Procedure
for the One-Pot Synthesis of Substituted 2-Aminothiophenes 3
A
mixture of carbonyl compound (3.0 mmol), nitrile (3.3 mmol), sulfur
(4.5 mmol), l-proline (0.3 mmol), and DMF (3.0
mL) in a 50 mL round bottom flask was stirred at 60 ˚C for
10-24 h. The crude product was directly purified through flash
chromatography to give the desired product 3.
The spectral data of all compounds 3a-o matched in all respects with reported
data.