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Synthesis of fluorinated furo- and pyrrolo[3,4-b]quinoxaline 4,9-dioxides

Svetlana Konstantinovna Kotovskaya 1
Svetlana Konstantinovna Kotovskaya
, 
Natalya Mikhailovna Perova 1
Natalya Mikhailovna Perova
,  , 
Oleg Nikolaevich Chupakhin 2
Oleg Nikolaevich Chupakhin
10.1070/MC1999v009n02ABEH001056
Published 1999-04-01
Communication , Volume 9, Issue 2, 76-77
9
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Kotovskaya S. K. et al. Synthesis of fluorinated furo- and pyrrolo[3,4-b]quinoxaline 4,9-dioxides // Mendeleev Communications. 1999. Vol. 9. No. 2. pp. 76-77.
GOST all authors (up to 50) Copy
Kotovskaya S. K., Perova N. M., Charushin V. N., Chupakhin O. N. Synthesis of fluorinated furo- and pyrrolo[3,4-b]quinoxaline 4,9-dioxides // Mendeleev Communications. 1999. Vol. 9. No. 2. pp. 76-77.
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TY - JOUR
DO - 10.1070/MC1999v009n02ABEH001056
UR - https://mendcomm.colab.ws/publications/10.1070/MC1999v009n02ABEH001056
TI - Synthesis of fluorinated furo- and pyrrolo[3,4-b]quinoxaline 4,9-dioxides
T2 - Mendeleev Communications
AU - Kotovskaya, Svetlana Konstantinovna
AU - Perova, Natalya Mikhailovna
AU - Charushin, Valery Nikolaevich
AU - Chupakhin, Oleg Nikolaevich
PY - 1999
DA - 1999/04/01
PB - Mendeleev Communications
SP - 76-77
IS - 2
VL - 9
ER -
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@article{1999_Kotovskaya,
author = {Svetlana Konstantinovna Kotovskaya and Natalya Mikhailovna Perova and Valery Nikolaevich Charushin and Oleg Nikolaevich Chupakhin},
title = {Synthesis of fluorinated furo- and pyrrolo[3,4-b]quinoxaline 4,9-dioxides},
journal = {Mendeleev Communications},
year = {1999},
volume = {9},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1999v009n02ABEH001056},
number = {2},
pages = {76--77},
doi = {10.1070/MC1999v009n02ABEH001056}
}
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Kotovskaya, Svetlana Konstantinovna, et al. “Synthesis of fluorinated furo- and pyrrolo[3,4-b]quinoxaline 4,9-dioxides.” Mendeleev Communications, vol. 9, no. 2, Apr. 1999, pp. 76-77. https://mendcomm.colab.ws/publications/10.1070/MC1999v009n02ABEH001056.

Abstract

The reaction of 5,6-difluorobenzofuroxane 1 with ethyl acetoacetate in the presence of triethylamine results in the formation of 2-methyl-3-ethoxycarbonyl-6,7-difluoroquinoxaline 1,4-dioxide 2 which was converted consequently into the bromomethyl 3 and acetoxymethyl 4 derivatives; hydrolysis of the latter with hydrochloric acid gave furo[3,4-b]quinoxaline 4,9-dioxide 5. Compound 3 was transformed by the action of ammonia and primary alkyl amines into 2-substituted 1,3-dihydro-2H-pyrrolo[3,4-b]quinoxaline 4,9-dioxides 6 and further into the corresponding 6-amino compounds 7 and 8.

References

1.
Progress in the chemistry of quinoxalineN-oxides andN,N′-dioxides
Kurasawa Y., Takada A., Kim H.S.
Journal of Heterocyclic Chemistry, 1995
2.
10.1070/MC1999v009n02ABEH001056_bib2
Cheesman
1979
3.
Synthesis and antibacterial activity of 1-hydroxy-1-methyl-1,3-dihydrofuro[3,4-b]quinoxaline 4,9-dioxide and related compounds
Dirlam J.P., Czuba L.J., Dominy B.W., James R.B., Pezzullo R.M., Presslitz J.E., Windisch W.W.
Journal of Medicinal Chemistry, 1979
4.
10.1070/MC1999v009n02ABEH001056_bib4
Musatova
Khim.-Farm. Zh., 1979
5.
GB Patent, 1,303,372, C07D, A61K, 1973 (Chem. Abstr., 1974, 81, 63674r).
6.
10.1070/MC1999v009n02ABEH001056_bib6
Bouzard
Antibiotics and Antiviral Compounds, 1993
7.
Hypoxia-Selective Agents Derived from Quinoxaline 1,4-Di-N-oxides
Monge A., Palop J.A., de Cerain A.L., Senador V., Martinez F.J., Sainz Y., Narro S., Garcia E., de Miguel C.
Journal of Medicinal Chemistry, 1995
8.
10.1070/MC1999v009n02ABEH001056_bib8
Kotovskaya
Zh. Org. Khim., 1998
10.
Photolysis of Some Quinoxaline-1,4-dioxides. A Method of Structural Assignment
J. Haddadin M., A. Jarrar A., S. Halawi S.
Heterocycles, 1976