113967-95-6Relevant articles and documents
A Comparison of Nucleophilic Reactions of 3-Benzenesulfonyloxyalloxazine and its 1-Methyl Analog.
Hamby, James M.,Bauer, Ludwig
, p. 1013 - 1024 (2007/10/02)
Reactions of 3-benzenesulfonyloxyalloxazine (1a) and its 1-methyl analog 1b with a number of nucleophilic reagents are reported.Relatively small nucleophiles, such as hydroxide ion, methanol, ethanol, methylamine, hydrazine and hydroxylamine converted 1a to 4-carboxy-s-triazoloquinoxalin-1(2H)-ones and the corresponding esters or amides.As the size of the amine increased from methylamine to ethylamine, dimethylamine, propylamine and isopropylamine, there were obtained 4-(carboxamido)-s-triazoloquinoxalin-1(2H)-ones, (1-carboxamido)imidazoloquinoxalines and 2,3-bis(ureido)quinoxalines.Sodium hydride or potassium cyanide in hot DMF degraded 1a to imidazoloquinoxaline.However, methylmercaptide and benzylmercaptide ions attacked the sulfonate group of 1a to form 3-hydroxyalloxazine. 1-Methyl-3-benzenesulfonyloxyalloxazine (1b) reacted with methanol, ethanol, 1-propanol, and to some degree 2-propanol, in the presence of triethylamine to furnish anhydro-1-hydroxy-3-methyl-4-(alkoxycarbonyl)-s-triazoloquinoxalinium hydroxides.However, sodium methoxide in methanol converted this starting material to a mixture of anhydro-1-hydroxy-3-methyl-s-triazoloquinoxalinium hydroxide and 1-methyl-3-hydroxyflavazole.A saturated aqueous solution of triethylamine transformed 1b to anhydro-1-hydroxy-3-methyl-s-triazoloquinoxalinium hydroxide, apparently via the corresponding unstable 4-carboxylic acid.The reactions of 1b with a number of aliphatic amines yielded either amides based on the above mesionic system or on the 3-carboxamido-2-quinoxalyl semicarbazide structure.The reaction of 1b with potassium cyanide furnished 1-methylimidazoloquinoxaline.Mechanisms to explain all of the degradations are advanced.
