Please use this identifier to cite or link to this item: https://scidar.kg.ac.rs/handle/123456789/10185
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dc.contributor.authorMarkovic, Svetlana-
dc.contributor.authorJoksović, Milan-
dc.contributor.authorBombicz P.-
dc.contributor.authorLeovac V.-
dc.contributor.authorMarković, Violeta-
dc.contributor.authorJoksović, Ljubinka-
dc.date.accessioned2021-04-20T15:05:58Z-
dc.date.available2021-04-20T15:05:58Z-
dc.date.issued2010-08-07-
dc.identifier.issn00404020-
dc.identifier.urihttps://scidar.kg.ac.rs/handle/123456789/10185-
dc.description.abstractThe structure of 5-hydroxy-3,5-dimethyl-1-S-methylisothiocarbamoyl-2- pyrazolinium iodide (HDMCPI), a cyclic intermediate for a 3-aminopyrazole derivative, was determined by means of X-ray analysis and spectroscopic techniques. In a treatment of HDMCPI in alkaline aqueous solution, 4-acetyl-3(5)-amino-5(3)-methylpyrazole (AAMP) was unexpectedly yielded. The reaction of HDMCPI was monitored by 1H and 13C NMR spectroscopy. It was shown that keto-imine tautomer appears as the only tautomeric form. Density functional theory explained the spontaneous formation of keto-imine tautomer, whose existence is the main condition for generating a carbanion in alkaline medium. The carbanion further undergoes cyclization and elimination of MeSH, thus yielding AAMP. In the reaction of acetylacetone with thiosemicarbazide instead of S-methylisothiosemicarbazide, there were no traces of AAMP. This result can be attributed to the absence of keto-imine form in the tautomeric equilibrium, which would provide the formation of a carbanion for a nucleophilic attack and further cyclization. © 2010 Elsevier Ltd. All rights reserved.-
dc.relation.ispartofTetrahedron-
dc.rightsrestrictedAccess-
dc.titleTheoretical study on structural and mechanistic aspects of synthesis of a 3-aminopyrazole derivative-
dc.typearticle-
dc.identifier.doi10.1016/j.tet.2010.05.093-
dc.identifier.scopus77955424413-
Appears in Collections:Faculty of Science, Kragujevac

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