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Tautomerism, regioisomerism, and cyclization reactions of acridinyl thiosemicarbazides

  • The regioselectivities of methyl- and phenylhydrazine with acridin-9-yl isothiocyanate (thus yielding thiosemicarbazides with acridine substituted on the urea-type side) were examined. Methythydrazine regioselectivity was high with the alpha-nitrogen atom overwhelmingly more nucleophilic than the beta-nitrogen atom; phenylhydrazine regioselectivity was poor but varied with the solvent and only in the case of ethanol was nucleophilic predominance of the alpha-nitrogen atom pronounced. Of note, whilst both phenyl thiosemicarbazides were present in solution only as spiro forms, the methyl product was present as an equilibrium mixture of open-chain and spiro thiosemicarbazides. Reactions on the NH2 blocked analogue of methyl acridin-9-ylthiosemicarbazide (1-isopropylidene-2- methylthiosemicarbazide) were also examined. Interestingly, present in the starting material itself was a structural motif of novelty wherein a triazolethione represented the major species of an equilibrium between cyclic and open-chain forms

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Author:Karel D. Klinka, Eva Balentova, Juraj Bernát, Jan Imrich, Martina Vavrusova, Erich Kleinpeter, Kalevi Pihlaja, Andreas Koch
Document Type:Article
Year of first Publication:2006
Year of Completion:2006
Release Date:2017/03/24
Source:Journal of heterocyclic chemistry. - ISSN 0022-152X. - 43 (2006), 3, S. 633 - 643
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert
Institution name at the time of publication:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Organische Chemie und Strukturanalytik