Synthesis and Cyclization of 2-Amino- and 2-Methyl-Substituted 1,3-Diaminobenzimidazolium Salts View Full Text


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Article Info

DATE

2015-02

AUTHORS

T. A. Kuz’menko, A. S. Morkovnik, L. N. Divaeva, G. S. Borodkin, V. V. Kuz’menko

ABSTRACT

N-Amination of 1-amino(alkylamino, benzylidenamino)-substituted 2-amino- and 2-methylbenzimid-azoles with O-picrylhydroxylamine gave the respective 1,2,3-triamino- and 1,3-diamino-2-methylbenz-imidazolium salts, which cyclized upon treatment with acetic anhydride/K2CO3 into previously unreported derivatives of N-amino[1, 2, 4]triazolo[1,5-а]benzimidazoles and N-aminopyrazolo-[1,5-а]benzimidazoles. The presence of С-acetyl substituent in the formed pyrazolo[1,5-а]benz-imidazoles was interpreted by quantum-chemical calculations as resulting from acylation of the intermediate methylene base, not tricyclic system. More... »

PAGES

1575-1585

References to SciGraph publications

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  • 1995-01. Heterocyclic analogs of pleiadiene. 63. Synthesis and crystal structure of 1-aminoperimidines in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 2004-02. Cyclization of 3-Ethoxycarbonylmethyl-, 3-Cyanomethyl-, and 3-Acetylmethyl-1-amino-2-methylbenzimidazolium Salts Effected by Acetic Anhydride in the Presence of a Base in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • 1992-12. Ring contraction of thia(seleno)diazine rings into pyrazoles in the reaction of 3-aryl-10-methyl-2H-1,3,4-thia(seleno)diazino[3, 2-a]benzimidazolium salts with bases in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 2014-05. 1-Amino-2-hydrazinobenzimidazole and its reactions with some carbonyl compounds in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • 1983-04. Tricyclic heteroaromatic ring systems IV. Synthesis and reactions of 4H-Pyrazolo[1,5-a]benzimidazole in MONATSHEFTE FÜR CHEMIE - CHEMICAL MONTHLY
  • 1992-02. 1-Amino-3-alkyl-2-(methylthio)benzimidazolium salts: synthesis, reaction with CH-acid anions, and conversion to pyrazolo[1,5-a]benzimidazole derivatives in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 2006-01. Synthesis and antimicrobial activity of some new 1-alkyl-2-alkylthio-1,2,4-triazolobenzimidazole derivatives in ARCHIVES OF PHARMACAL RESEARCH
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    http://scigraph.springernature.com/pub.10.1007/s10593-014-1627-8

    DOI

    http://dx.doi.org/10.1007/s10593-014-1627-8

    DIMENSIONS

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