Quinoxalines. Part 13: Synthesis and mass spectrometric study of aryloxymethylquinoxalines and benzo[b]furylquinoxalines |
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Authors: | Ines Starke Vladimir V. Ovcharenko Erich Kleinpeter |
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Affiliation: | a Chemisches Institut der Universität Potsdam, Postfach 60 15 53, D-14415 Potsdam, Germany b Department of Chemistry, University of Turku, FIN-20014 Turku, Finland |
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Abstract: | A series of new aryloxymethylquinoxalines, benzo[b]- and naphtho[2,1-b]furylquinoxalines, possessing potential biological activity, was prepared, characterized by IR and NMR spectroscopy and their electron ionization (EI) mass spectra studied in detail. The aryloxymethylquinoxalines were obtained by reacting halogenomethylquinoxalines with bifunctional O-nucleophiles. The benzo[b]furylquinoxalines and naphtho[2,1-b]furylquinoxalines were prepared via two routes, which differed in the order of the two cyclization steps involved in the syntheses. The composition of the ions obtained by EI mass spectrometry were determined by accurate mass measurements and the fragmentation pathways clarified by B/E linked scans and collision induced dissociation. The mass spectrometric behaviour of the compounds studied as to the possible loss of OH radicals proved to be very characteristic. |
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Keywords: | Aryloxymethylquinoxalines Benzo[b]furylquinoxalines Halogenomethylquinoxalines Mass spectrometric behaviour Structure-fragmentation relationship OH 0" alt=" radical dot" src=" http://cdn.els-cdn.com/sd/entities/rad" class=" glyphImg" > Aryl migration |
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