80009-72-9Relevant academic research and scientific papers
Formation of Quinoxaline and Benzimidazole Derivatives from Methylpentoses by the Reaction with o-Phenylenediamine
Morita, Naofumi,Daido, Yoshiyuki,Takagi, Masanosuke
, p. 2753 - 2762 (2007/10/02)
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 deg C.The total yield of the products as sugar was about 80percent from either rhamnose or fucose.The structure of RHA-I was (2'S)-2-methyl-3-(2'-hydroxypropyl)quinoxaline; RHA-II, (2'R,3'S)-2-(2',3'-dihydroxybutyl)quinoxaline; RHA-III, (1'S,2'S,3'S)-2-(1',2',3'-trihydroxybutyl)quinoxaline; RHA-III', 2-(L-ribo-1',2',3'-trihydroxybutyl)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, (2'S,3'S)-2-(2',3'-dihydroxybutyl)quinoxaline; FUA-III, (1'R, 2'R, 3'S)-2-(1', 2', 3'-trihydroxybutyl)quinoxaline2-(L-xylo-1', 2', 3'-trihydroxybutyl)quinoxaline; 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.
