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Structural revision of products resulting from the reaction of methylhydrazine with acridin-9-yl isothiocyanate due to unexpected acridinyl migration And further reactions

  • The reaction of methyl acridin-9-ylthiosemicarbazide under basic conditions with methyl bromoacetate resulted in a 1,3-thiazolin-4-one structure as provided by X-ray crystallography. The structure forced a re-evaluation of the reactant methyl acridin-9-ylthiosemicarbazide, originally thought to be 2-methyl 4-acridin-9-ylthiosemicarbazide based on synthetic expectations, but which when examined by X-ray crystallography was found to be in fact the isomeric 2- methyl 1-acridin-9-ylthiosemicarbazide resulting from rearrangement via a spiro form which it is in equilibrium with in solution. The product resulting from reaction with methyl iodide was also studied and the previously reported semicarbazide produced by reaction with MNO was re-examined. In both cases, the 1,2 isomer rather than the 2,4 isomer was found to be present based on the sign of the 3JCH3,N11 coupling. Full characterization of the compounds was rendered by 1H, 13C, and 15N solution-state NMR, and in the solid state, by both 13C and 15N NMR.

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Author:Karel D. Klinka, Eva Balentova, Juraj Bernát, Ján Imrich, Martina Vavrusová, Kalevi Pihlaja, Andreas Koch, Erich Kleinpeter, Alexandra Kelling, Uwe SchildeORCiDGND
Document Type:Article
Year of first Publication:2006
Year of Completion:2006
Release Date:2017/03/24
Source:ARKIVOC. - ISSN 1551-7004. - 16 (2006), S. 93 - 108
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Nicht referiert