Quinoxalino[2,3- c ]cinnolines and their 5- N -oxide: Alkoxylation of methyl-substituted quinoxalino[2,3- c ]cinnolines to acetals and orthoesters

Makhluf J. Haddadin, Mirna El-Khatib, Tharallah A. Shoker, Christine M. Beavers, Marilyn M. Olmstead, James C. Fettinger, Kelli M. Farber, Mark J. Kurth

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Abstract

We report the alkoxylation of methyl-substituted quinoxalino[2,3-c] cinnolines to give acetals and orthoesters in high yields. Routes to the precursors of this alkoxylation reaction as well as other quinoxalino[2,3-c] cinnoline and their 5-oxide derivatives are reported. Most of these quinoxalino[2,3-c]cinnolines were prepared by cyclization of the corresponding 2-amino-3-(2-nitrophenyl)quinoxaline, which, in turn, result from an unusual Beirut reaction from benzofurazan oxides plus 2-nitrobenzylcyanides. Mechanistic explanations for these intriguing reactions are presented.

Original languageEnglish (US)
Pages (from-to)8421-8427
Number of pages7
JournalJournal of Organic Chemistry
Volume76
Issue number20
DOIs
StatePublished - Oct 21 2011

ASJC Scopus subject areas

  • Organic Chemistry

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    Haddadin, M. J., El-Khatib, M., Shoker, T. A., Beavers, C. M., Olmstead, M. M., Fettinger, J. C., Farber, K. M., & Kurth, M. J. (2011). Quinoxalino[2,3- c ]cinnolines and their 5- N -oxide: Alkoxylation of methyl-substituted quinoxalino[2,3- c ]cinnolines to acetals and orthoesters. Journal of Organic Chemistry, 76(20), 8421-8427. https://doi.org/10.1021/jo201687x