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Issue 4, 2001
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A stereoselective route to 3-methyl-2-methylsulfanyl-5- ylidene-3,5-dihydroimidazol-4-one derivatives and precursor of Leucettamine B

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Abstract

A range of aromatic aldehydes 8a-f was tested in Knoevenagel reaction with 3-methyl-2-methylsulfanyl-3,5- dihydroimidazol-4-one 7 and piperidine as catalyst using solvent-free conditions under microwave-mediated conditions. The results of these condensations were compared to classical procedure in methylene chloride. This efficient, simple and environmentally friendly methodology gave respectively and stereoselectively the (5Z)-5-arylidene-3,5-dihydroimidazol-4-ones 9ae in good yields (78–95%) and the precursor 9f of Leucettamine B. Then, these solvent-less condition reactions have been also applied to cyclic ketones 10ad, acetone 12a and actived ketones 12b,c. The 1H, 13C NMR spectrum of some representative 5-ylidene-3,5-dihydroimidazol-4-ones are also reported.

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Publication details

The article was received on 28 Feb 2001 and first published on 25 Jun 2001


Article type: Paper
DOI: 10.1039/B101928G
Green Chem., 2001,3, 165-169

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    A stereoselective route to 3-methyl-2-methylsulfanyl-5- ylidene-3,5-dihydroimidazol-4-one derivatives and precursor of Leucettamine B

    J. R. Chérouvrier, J. Boissel, F. Carreaux and J. P. Bazureau, Green Chem., 2001, 3, 165
    DOI: 10.1039/B101928G

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