TY  - JOUR
A1  - Klinka, Karel D.
A1  - Balentova, Eva
A1  - Bernát, Juraj
A1  - Imrich, Jan
A1  - Vavrusova, Martina
A1  - Kleinpeter, Erich
A1  - Pihlaja, Kalevi
A1  - Koch, Andreas
T1  - Tautomerism, regioisomerism, and cyclization reactions of acridinyl thiosemicarbazides
N2  - 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
Y1  - 2006
UR  - https://publishup.uni-potsdam.de/frontdoor/index/index/docId/11974
UR  - http://www3.interscience.wiley.com/journal/121521817/toc
SN  - 0022-152X
ER  -