- A new facile, efficient synthesis and structure peculiarity of quinoxaline derivatives with two benzimidazole fragments
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A highly efficient and versatile method for the synthesis of quinoxaline derivatives with two benzimidazole fragments have been developed on the basis of the ring contraction of 3-(benzimidazo-2-yl)quinoxalin-2(1H)-one with 1,2-diaminobenzene and its various types of substituted and condensed derivatives. Owing to the inter- and intramolecular processes, involving self association, proton exchange, conformational, and/or tautomeric exchanges between several forms for most of the bis-benzimidazolylquinoxalines signals of bridged and neighboring carbon atoms and the hydrogen atoms of the neighboring carbon atoms of benzimidazole fragments in the NMR spectra are broadened. The conjugation between the benzimidazole fragments and the quinoxaline core of the molecules is increased from the quinoxaline derivative (10c) to its thiadiazol[f]- (17) and pyrrolo[a]-(19) annulated derivatives, resulting in a greater planarity of the molecule as a whole.
- Mamedov, Vakhid A.,Zhukova, Nataliya A.,Syakaev, Victor V.,Gubaidullin, Aidar T.,Beschastnova, Tat'Yana N.,Adgamova, Dil'Bar I.,Samigullina, Aida I.,Latypov, Shamil K.
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supporting information
p. 1403 - 1416
(2013/02/23)
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- The reactions of benzofuroxan with carbonyl compounds on the surface of solid catalysts
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The cyclocondensations of benzofuroxan 1a with carbonyl compounds were smoothly and efficiently carried out by the adsorption of the components on the surface of silica gel or a molecular sieve to form a 2,3-disubstituted quinoxaline 1,4-dioxide. When the
- Takabatake,Hasegawa,Hasegawa
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p. 1477 - 1480
(2007/10/02)
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- An Improved and Efficient Synthesis of Quinoxalinecarboxamide 1,4-Dioxides from Benzofuroxan and Acetoacetamides in the Presence of Calcium Salts
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An improved and efficient method for the preparation of the title compounds 3 is described.Thus, quinoxalinecarboxamide 1,4-dioxides 3 are synthesized in high yields by reaction of benzofuroxan 1 with acetoacetamides 2 in the presence of catalytic amounts of calcium salts and ethanolamine.The reaction is assumed to involve a chelate mechanism with 4 as intermediate.Side reactions are studied by means of HPLC and TLC.
- Stumm, G.,Niclas, H.-J.
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p. 736 - 744
(2007/10/02)
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- A New Synthesis of 2,3-Disubstituted Quinoxaline 1,4-Dioxide Catalyzed by Molecular Sieves
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The syntheses of 2,3-disubstituted quinoxaline 1,4-dioxides are smoothly and efficiently carried out by the adsorption of the components on molecular sieve 3A (powder) from benzofuroxan 1 and 1,3-diketones, 3-oxoalkanoic esters, or 3-oxoalkanamides 2.
- Takabatake, Tohru,Hasegawa, Minoru
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p. 529 - 530
(2007/10/02)
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