M. Cai
1985
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Journal
Acta Chimica Sinica
Abstract
The preparation and chemical transformations of ethyl N-[5′-(3′-methylmercapto- 6′-ethoxycarbonyl)-1′,2′,4′-triazinyl]-3-methylmercapto-5-oxo-1,2,4-triazine-6- carboxylate(3a)were reported.3a was obtained by treating ethyl 3-methylmercapto-5- oxo-1,2,4-triazine-6-carboxylate(1)in the presence of pyridine withp-toluenesulfonyl chloride in benzene and then water. 3a reacted with a series of aromatic amines in hot ethanol to give ethyl 5-substituted amine-3-methylmercapte-1,2,4-triazine-6-carboxylates(5,6,7,8).No reaction took place when isobutylamine was used.When compound 3a was reacted with p-toluidine in hot ethanol,ethyl 3-toluidino-5-hydroxy-1,2,4-triazine-6-carboxylate(9)and ethyl 3,5-ditoluidino-1,2,4-triazine-6-carboxylate(10)were obtained in addition to the ethyl 5-substituted amino-3-methylmercapto-1,2,4-triazine-6-carboxylate (8). When compound 3a was reacted with hydrazine(90%),the N,N′-bis[5-(3-methyl- mercapto-6-ethoxycarbonyl)-1,2,4-triazinyl]-hydrazine(11)was obtained. Compound 3a reacted with p-cresol,guaiacol,p-methoxyphenol,p-nitrophenol and o-nitrophenol in ethanolic pyridine at room temprature to give the corresponding ethyl 3-methylmercapto-5-aryloxy-1,2,4-triazine-6-carboxylate(12,13,14,15,16).