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Quinoxalines XV : convenient synthesis and structural study of pyrazolo[1,5-alpha]quinoxalines

  • A series of aryloxymethylquinoxaline oximes, hitherto unknown and synthesized from the corresponding aldehydes, afforded in only one step pyrazolo[1,5-;]quinoxalines in the presence of acetic anhydride at high temperatures. A formal [3,5]-sigmatropic rearrangement was proposed as the mechanistic rationale for this unprecedented transformation. Saponification with potassium hydroxide furnished the free phenol derivatives which were studied by NMR spectroscopy and accompanying theoretical DFT calculations, establishing intramolecular hydrogen bonding and the spatial magnetic properties. Additionally, mass spectrometric fragmentation was investigated by B/E-linked scans and collision-induced dissociation experiments. The fragmentation pattern devoted a new gas phase rearrangement process, which proved to be unique and characteristic for pyrazolo[1,5-;]quinoxalines.

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Author details:Gerhard Sarodnick, Torsten LinkerORCiDGND, Matthias HeydenreichORCiD, Andreas KochORCiDGND, Ines StarkeORCiD, Sylvia Fürstenberg, Erich KleinpeterORCiDGND
URL:http://pubs.acs.org/journal/joceah
DOI:https://doi.org/10.1021/Jo802398g
ISSN:0022-3263
Publication type:Article
Language:English
Year of first publication:2009
Publication year:2009
Release date:2017/03/25
Source:The Journal of organic chemistry : JOC. - ISSN 0022-3263. - 74 (2009), 3, S. 1282 - 1287
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer review:Referiert
Institution name at the time of the publication:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Organische Chemie und Strukturanalytik
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