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Studies on pyrazine derivatives, XLVI: The synthesis of new pyrazine derivatives with N?-(pyrazine-2-carbonyl)-hydrazinecarbodithioic acid methyl ester usage
4-Omega-alkylsubstituted derivatives of 1,2,4-triazole-2-thiones 2-7 were obtained using the high reactivity of N?-(pyrazine-2-carbonyl)- hydrazinecarbodithioic acid methyl ester 1 towards amines. In the reaction with cysteamine 1,3-thiazaethylene-1,2,4-triazole 8 formed. Aromatic amines and N-aminocycloalkylamines gave thiosemicarbazide derivatives 9-12 under the same conditions. The solution of sodium hydroxide caused the decomposition of compounds 11 and 12 and resulted in 4-piperidino- and 4-morpholino- thiosemicarbazides 13 and 14. Compounds 11 and 12 were cyclized to appropriate 4-substituted 1,2,4-triazole-2-thiones 16 and 17 under the influence of DBU or potassium carbonate solution. The heating of derivative 12 with sulfuric acid led to disubstituted 1,3,4-thiadiazole 18. Copyright Taylor & Francis Group, LLC.
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Reference£º
Piperidine – Wikipedia,
Piperidine | C5H4859N – PubChem