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Regioselective carbon-carbon bond formation at C2 of 1,3-thiazole by reaction of n-ethoxycarbonylthiazolium chloride with C-nucleophiles

โœ Scribed by Alessandro Dondoni; Tiziano Dall'Occo; Giancarlo Fantin; Marco Fogagnolo; Alessandro Medici


Book ID
104242286
Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
231 KB
Volume
25
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


N-Ethoxycarbonylthiazolium chloride generated in situ from 1,3-thiazo-le and ethyl chloroformate, treated with lithium carbanions of esters, Grignard reagents, silyl enol ethers and esters, undergo nucleophilic addition at C2 affording the corresponding 2-substituted N-ethoxycarbonylthiazolines.

We have recently described' the reactions of 1,3-thiazoles t-1) (X = H, SiMe3) with C-electrophiles (E), namely ketenes, acyl chlorides and aldehydes, to give


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