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Pellizzari reaction : ウィキペディア英語版
Pellizzari reaction
The Pellizzari reaction was discovered in 1911 by Guido Pellizzari, and is the organic reaction of an amide and a hydrazide to form a 1,2,4-triazole.〔Pellizzari, G. ''Gazz. Chim. Ital.'' 1911, ''41'', 20.〕
The product is similar to that of the Einhorn-Brunner reaction, but the mechanism itself is not regioselective.
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==Mechanism==
The mechanism begins by the nitrogen in the hydrazide attacking the carbonyl carbon on the amide to form compound 3. The negatively charged oxygen then abstracts two hydrogens from neighboring nitrogens in order for a molecule of water to be released to form compound 5. The nitrogen then performs an intramoleculer attack on the carbonyl group to form the five-membered ring of compound 6. After another proton migration from the nitrogens to the oxygen, another water molecule is released to form the 1,2,4-triazole 8. 〔 〕
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