 ISSN 0235-7216
ISSN 2424-4538 (online)
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2012 m. Nr. 1
 Synthesis of azolethione derivatives from 3-(phenylamino)propanehydrazide
Ingrida TUMOSIENĖ, Zigmuntas Jonas BERESNEVIČIUS
Heating of 3-(phenylamino)propanehydrazide with ethyl xanthogenate provided potassium salt of carbodithioate, which under the action of hydrochloric or sulphuric acid was cyclized to 5-[2-(phenylamino)ethyl]-2,3-dihydro-1,3,4-oxadiazole-2-thione or 5-[2-(phenylamino)ethyl]-2,3-dihydro-1,3,4-thiadiazole-2-thione. In the reaction with phenacyl bromide it was transformed into N-(4-phenyl-2-thioxo-2,3-dihydro-1-, 3-tiazol-3-yl)-3-(phenylamino)propanamide and, under treatment with hydrazine, gave 4-amino-3-[2-(phenylamino)ethyl]-4,5-dihydro-1H-1,2,4-triazole-5-thione, which subsequently underwent condensation reaction with phenacyl bromide to give N-[2-(6- phenyl-7H-[1,2,4]triazol[3,4-b][1,3,4]-3-yl)ethyl]aniline.
Keywords: hydrazide, 1,2,4-triazolethione, 1,3,4-oxadiazolethione, 1,3,4-thiadiazolethione, tetraazabicyclononatriene, cyclization
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