Use of Tetramethylthiuram Disulfide in Synthesis of Nitrogen-containing Heterocyclic Compounds |
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| Authors: | A M Demchenko V A Yanchenko V V Kisly M S Lozinskii |
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| Institution: | (1) T. G. Shevchenko Chernigov State Pedagogical University, Chernigov, 14038, Ukraine;(2) Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, 02094, Ukraine |
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| Abstract: | We have developed a method for synthesis of aryl isothiocyanates by means of thiocarbamoylation of aromatic amines by tetramethylthiuram disulfide followed by degradation of the intermediate N(1)-aryl-N,N-dimethylthiourea by concentrated HCl. We have shown that thiocarbamoylation of 4-amino-5-ethyl-4H-1,2,4-triazole-3-thiol occurs at the 2 position of the triazole ring, while thiocarbamoylation of 4-amino-3-methyl-6-phenyl-4,5-dihydro-1,2,4-triazin-5-one leads to the dihetaryl-substituted thiourea. We consider the possibility of using N(1)-aryl-N,N-dimethylthioureas as analogs of isothiocyanates in reactions with N-nucleophiles.__________Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 775–780, May, 2005. |
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| Keywords: | N(2)-(3-chloro-2-methylphenyl)-2-amino-5 6-dihydro-4H-1 3-thiazine 4-amino-3-methyl-6-phenyl-4 5-dihydro-1 2 4-triazin-5-one N(1)-aryl-N N-dimethylthioureas aryl isothiocyanates N-aryl-N(1)-(5-mercapto-3-methyl-4H-1 2 4-triazol-4-yl)thioureas 6-(4-bromophenylamino)-3-methyl[1 2 4]-triazolo[3 4-b][1 3 4]thiadiazole tetramethylthiuram disulfide |
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