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

doi:10.1021/jo201687x

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

Chemistry

Research output: Contribution to journal › Article

10 Scopus citations

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 language	English (US)
Pages (from-to)	8421-8427
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	76
Issue number	20
DOIs	https://doi.org/10.1021/jo201687x
State	Published - 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

Quinoxalino[2,3- c ]cinnolines and their 5- N -oxide : Alkoxylation of methyl-substituted quinoxalino[2,3- c ]cinnolines to acetals and orthoesters. / Haddadin, Makhluf J.; El-Khatib, Mirna; Shoker, Tharallah A.; Beavers, Christine M.; Olmstead, Marilyn M.; Fettinger, James C.; Farber, Kelli M.; Kurth, Mark J.

In: Journal of Organic Chemistry, Vol. 76, No. 20, 21.10.2011, p. 8421-8427.

Research output: Contribution to journal › Article

Haddadin, Makhluf J. ; El-Khatib, Mirna ; Shoker, Tharallah A. ; Beavers, Christine M. ; Olmstead, Marilyn M. ; Fettinger, James C. ; Farber, Kelli M. ; Kurth, Mark J. / Quinoxalino[2,3- c ]cinnolines and their 5- N -oxide : Alkoxylation of methyl-substituted quinoxalino[2,3- c ]cinnolines to acetals and orthoesters. In: Journal of Organic Chemistry. 2011 ; Vol. 76, No. 20. pp. 8421-8427.

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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.",

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AU - Haddadin, Makhluf J.

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AU - Shoker, Tharallah A.

AU - Beavers, Christine M.

AU - Olmstead, Marilyn M.

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AB - 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.

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