Formation of Quinoxaline and Benzimidazole Derivatives from Methylpentoses by the Reaction with o-Phenylenediamine
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概要
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Quinoxaline and benzimidazole derivatives obtained from L-rhamnose and L-fucose under deoxygenated, weakly acidic, heated conditions were studied using GLC, HPLC, and NMR. Four quinoxalines and one benzimidazole were obtained from L-rhamnose (RHA-I, II, III, III, and IV) and L-fucose (FUA-I, II, III, IV, and V) in an acidic solution (MeOH-AcOH-H2O= 8:1:2) at 80°C. The total yield of the products as sugar was about 80%from either rhamnose or fucose. The structure of RHA-I was (2S)-2-methyl-3-(2-hydroxypropyl) quinoxaline; RHA-II, (2R, 3S)-2-(2, 3-dihydroxybutyl) quinoxaline; RHA-III, (1S, 2S, 35)-2-(1, 2, 3-trihydroxybutyl) quinoxaline [2-(L-arabino-1, 2, 3-trihydroxybutyO) quinoxaline]; RHA-III , 2-(L-ribo- trihydroxybutytl) quinoxaline; and RHA-IV, 2-(L-manno-1, 2, 3, 4-tetrahydroxypentyl)- benzimidazole, and the structure of FUA-I was the same as RHA-I; FUA-II, (2S, 3S)-2-(2, 3- dihydroxybutyl) quinoxaline; FUA-III, (1R, 2R, 3S)-2-(1, 2, 3-trihydroxybutyl)quinoxaline [2-(L-xylo-1, 2, 3-trihydroxybutytyquinoxaline; FUA-IV, 2-(L-lyxo-1, 2, 3-trihydroxybutyl)- quinoxaline; and FUA-V, 2-(L-galacto-1, , 2, 3, 4-tetrahydroxypentyl) benzimidazole. These results suggest no significant difference for the pathways of quinoxaline and benzimidazole formation between L-rhamnose and L-fucose. Possible pathways are proposed for each sugar.
- 社団法人 日本農芸化学会の論文
著者
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MORITA Naofumi
Department of Agricultural Chemistry, College of Agriculture, University of Osaka Prefecture
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DAIDO Yoshiyuki
Department of Agricultural Chemistry, College of Agriculture, University of Osaka Prefecture
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Takagi Masanosuke
Department o f Agricultural Chemistry, College o f Agriculture, University
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