Abstract
The reaction of
6-amino-4-hydroxy-1-methylpyrimidine-2(1H)-thione (3) with hydrazine is shown
to follow at least three pathways to give 4-
amino-5-hydrazino-1,2,4-triazole-3-thiol (1), 5-hydrazino-pyrazol-3- ol(5; R = NH2), (4-amino-5-mercapto-1,2,4-triazol-3-yl)acetohydrazide
(4) and triamino-guanidine (6). Similarly,
4,6-dihydroxy-1- methylpyrimidine-2(1H)-thione (18) yields (1) and malonyl dihydrazide (19), and (4). By contrast
4,6-diamino-1-methylpyrimidine-2(1H)-thione (21) does not follow any of these
pathways. Formation of (4) represents a new type of ring transformation of
pyrimidines. Mechanisms of the reactions are discussed.
Cited by
21 articles.
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1. Potassium carbonate mediated unusual transformation of 2,3-dihydroquinazolinone via cascade reaction;Tetrahedron Letters;2013-11
2. 6-(4-Bromophenyl)-3-methyl-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine;Acta Crystallographica Section E Structure Reports Online;2012-05-12
3. Chemical Abstract and Journal References for 1,2,4-Triazoles;Chemistry of Heterocyclic Compounds: A Series Of Monographs;2008-01-02
4. References;Chemistry of Heterocyclic Compounds: A Series Of Monographs;2008-01-02
5. References;Chemistry of Heterocyclic Compounds: A Series Of Monographs;2008-01-02