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.
Document Type:
Article
Language: English
Citation:
S. K. Kotovskaya, N. M. Perova, V. N. Charushin, O. N. Chupakhin, “Synthesis of fluorinated furo- and pyrrolo[3,4-b]quinoxaline 4,9-dioxides”, Mendeleev Commun., 9:2 (1999), 76–77
Linking options:
https://www.mathnet.ru/eng/mendc4533
https://www.mathnet.ru/eng/mendc/v9/i2/p76
This publication is cited in the following 9 articles:
Fatemeh Hajishaabanha, Shabnam Shaabani, Ahmad Shaabani, “Synthesis of furan-fused quinoxaline tetracyclic scaffolds via a three-component isocyanide-based reaction”, Res Chem Intermed, 42:5 (2016), 4109
Comprehensive Organic Name Reactions and Reagents, 2010, 303
A. A. Layeva, E. V. Nosova, G. N. Lipunova, V. N. Charushin, “Fluoroarenes in the synthesis of benzoannulated nitrogen-containing heterocycles”, Russ Chem Bull, 57:5 (2008), 947
Mercedes González, Hugo Cerecetto, Antonio Monge, Topics in Heterocyclic Chemistry, 11, Bioactive Heterocycles V, 2007, 179
E. V. Nosova, N. N. Mochul'skaya, S. K. Kotovskaya, G. N. Lipunova, V. N. Charushin, “Fluorinated benzazoles and benzazines”, Heteroatom Chemistry, 17:6 (2006), 579
S. K. Kotovskaya, V. N. Charushin, N. M. Perova, M. I. Kodess, O. N. Chupakhin, “Intramolecular Nucleophilic Substitution of Hydrogen in (Quinoxalinyl‐2)aminovinyl Derivatives as a New Approach to Pyrrolo‐ and Indolo[2,3‐b]quinoxalines”, Synthetic Communications, 34:14 (2004), 2531
V. N. Charushin, S. K. Kotovskaya, N. M. Perova, O. N. Chupakhin, “Pyrido[2,3-b]- and pyrimido[4,5-b]quinoxalines: the first fluorine-containing derivatives”, Mendeleev Commun., 11:2 (2001), 54–56
Svetlana K. Kotovskaya, Natalya M. Perova, Valerii N Charushin, Oleg N. Chupakhin, “ChemInform Abstract: Synthesis of Fluorinated Furo‐ and Pyrrolo[3,4‐b]quinoxaline 4,9‐Dioxides.”, ChemInform, 30:37 (1999)
O. N. Chupakhin, S. K. Kotovskaya, N. M. Perova, Z. M. Baskakova, V. N. Charushin, “Synthesis of new fluorine-containing derivatives of quinoxaline 1,4-dioxides and condensed systems derived from them”, Chem Heterocycl Compd, 35:4 (1999), 459
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