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- W2035990170 abstract "Kinetic studies on the Hinsberg condensation were performed trying to improve yields and achieve regio-selectivity in the attainment of benzene-substituted 3-methylquinoxalin-2(1H)-ones. The course of the reactions between o-phenylenediamine (o-PDA) and substituted o-PDA with pyruvic acid (2a) or ethyl pyruvate (2b) were followed by uv spectrophotometry at different pH values. The formation of 3-methylquinoxalin-2(1H)-one (6a) was improved using sulphuric acid-water mixtures, in which the reaction proceeded by a different mechanism. 3-Methyl-7-methoxyquinoxalin-2(1H)-one (7b) was regioselectively synthesized independently of the pH of the reaction media. Reaction of 2-amino-4-methylamine (1c) with 2a or 2b led to a mixture of 6 and 7-quinoxalinone isomers, 6c and 7c, while 2-amino-4-nitroaniline (1d) and 2,4-diaminoaniline (1e) with 2a or 2b did not afford the heterocycle. In every case reactions with 2a were 100–1000 times faster than those with 2b. Mechanisms are proposed trying to account for the experimental results." @default.
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- W2035990170 date "1987-11-01" @default.
- W2035990170 modified "2023-09-27" @default.
- W2035990170 title "Kinetic study on the anelation of heterocycles.<b>1</b>. Quinoxalinone derivatives synthesized by hinsberg reaction" @default.
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- W2035990170 doi "https://doi.org/10.1002/jhet.5570240651" @default.
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