Аннотация:
Reactions of 7-(X)-substituted ethyl 1-amino-4-oxo-1,4-dihydroquinoline-3-carboxylates (1a-c; X = F, Cl and 4-methylpiperazin-1-yl) with mono- and di-ketones have been studied. Treatment of 1a; X = F with cyclopentanone and cyclopentanone in acetic acid resulted in the corresponding azomethynes; α-dicarbonyl compounds such as glyoxal, glyoxylic acid or ethyl pyruvate caused desamination of 1a into ethyl, 6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate, while reactions of 1a-c with acetoacetone resulted in tricyclic 7-fluoro-4-oxopyrazolo[1,5-a]quinoline-4-carboxylic acids
Тип публикации:
Статья
Язык публикации: английский
Образец цитирования:
O. N. Chupakhin, Yu. A. Azev, S. G. Alexeev, S. V. Shorshnev, E. Tsoi, V. N. Charushin, “Reactions of N-Aminoquinolones with Ketones: A New Approach to the Synthesis of Tricyclic 6-Fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acids”, Mendeleev Commun., 2:4 (1992), 151–153
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https://www.mathnet.ru/rus/mendc5451
https://www.mathnet.ru/rus/mendc/v2/i4/p151
Эта публикация цитируется в следующих 10 статьяx:
A. A. Boteva, O. P. Krasnykh, “The methods of synthesis, modification, and biological activity of 4-quinolones (review)”, Chem Heterocycl Comp, 45:7 (2009), 757
V. N. Charushin, O. N. Chupakhin, “Nucleophilic aromatic substitution of hydrogen and related reactions”, Mendeleev Commun., 17:5 (2007), 249–254
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
El-Sayed H El-Ashry, El-Sayed I Ibrahim, Advances in Heterocyclic Chemistry, 84, 2003, 71
Yu. A. Azev, E. Lork, D. Gabel, T. Duelcks, “New way of the reaction of 1-amino-6,7-difluoro-4-oxoquinolyl-3-ethylcarboxylate with acetoacetone”, Mendeleev Commun., 13:4 (2003), 184–185
E. Tsoi, V. N. Charushin, E. V. Nosova, G. N. Lipunova, A. V. Tkachev, “New approach to [a]-fused fluoroquinolones: the synthesis of 5-oxo-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinolines”, Mendeleev Commun., 11:2 (2001), 53–54
David Barrett, Hiroshi Sasaki, Takayoshi Kinoshita, Akihiko Fujikawa, Kazuo Sakane, “A novel synthesis of the pyrazolo[1,5-a]quinoline ring system. New N1-C2 bridged DNA gyrase inhibitors via a novel tandem 1,4-conjugate addition-Michael [3+2] annulation process”, Tetrahedron, 52:25 (1996), 8471
Nucleophilic Aromatic Substitution of Hydrogen, 1994, 287
O. N. CHUPAKHIN, YU. A. AZEV, S. G. ALEXEEV, S. V. SHORSHNEV, E. TSOI, V. N. CHARUSHIN, “ChemInform Abstract: Reactions of N‐Aminoquinolones with Ketones: A New Approach to the Synthesis of Tricyclic 6‐Fluoro‐4‐oxo‐1,4‐dihydroquinoline‐3‐ carboxylic Acids.”, ChemInform, 24:15 (1993)
Yu. A. Azev, S. V. Shorshnev, S. G. Alexeev, V. N. Charushin, O. N. Chupakhin, “ipso-Substitution of an Acyl group in Reactions of 3-Acyl-substituted Ethyl 7,8-Difluoro-5-oxo-5,9a-dihydropyrazolo[1,5-a]quinoline-4-carboxylates with Electrophilic Reagents”, Mendeleev Commun., 3:3 (1993), 99–100
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