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DOI: 10.1055/s-0030-1258958
Synthesis of Quinoxalines via Ru/C Benzoin Oxidation and Diamine Condensation
V. K. Akkilagunta, V. P. Reddy, R. R. Kakulapati*
Indian Institute of Chemical Technology, Hyderabad, India
Publikationsverlauf
Publikationsdatum:
22. November 2010 (online)
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Significance
Reported is the synthesis of quinoxalines through the in situ oxidation of benzoins to 1,2-diketones and subsequent condensation with diamines. Although this reaction is not unknown, the oxidation system in this case used Ru/C, randomly methylated β-cyclodextrins (Ra-Me-β-CD), and an oxygen atmosphere with water as solvent (named as biomimetic conditions). For a reaction of 1 mmol of substrate, 300 mg of Ra-Me-β-CD was used. Ra-Me-β-CD was used to increase the dispersion of the supported ruthenium catalyst in water, thus increasing the activity of the catalyst. The oxidation does not proceed in the absence of Ra-Me-β-CD and evidence of complex formation between Ra-Me-β-CD and benzyl alcohol was obtained through NOESY studies.