ON THE REGIOSELECTIVITY IN THE HURD-MORI REACTION
Heterocycles(1993)
Abstract
Various alpha-substituted (Y) acetone hydrazones were subjected to the Hurd-Mori reaction to give the 4-methyl-5-Y-substituted 1,2,3-thiadiazoles and/or 4-Y-CH2 derivatives. The ratio of the two products changed drastically depending on the kind of the substituent Y and was parallel to the relative rate of enolization of the two alpha-carbons in the parent ketones.
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Key words
Cross-Coupling Reactions
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