A comparison of nucleophilic reactions of 3-benzenesulfonyloxyalloxazine and its 1-methyl analog was written by Hamby, James M.;Bauer, Ludwig. And the article was included in Journal of Heterocyclic Chemistry in 1987.Related Products of 49679-45-0 This article mentions the following:
Reactions of 3-benzenesulfonyloxyalloxazines I (R = H, Me) with a number of nucleophilic reagents are reported. Relatively small nucleophiles, such as HO–, MeOH, EtOH, MeNH2, N2H4, and HONH2, converted I (R = H) to 4-carboxy-s-triazolo[4,3-a]quinoxalin-1(2H)-ones and the corresponding esters ar amides. As the size of the amine increased from MeNH2 to EtNH2, Me2NH2, PrNH2, and Me2CHNH2, there were obtained 4-(carboxamido)-s-triazolo[4,3-a]quinoxalin-1(2H)-ones, (1-carboxamido)imidazolo[4,5-b]quinoxalines, and 2,3-bis(ureido)quinoxalines. NaH or KCN in hot DMF degraded I (R = H) to imidazolo[4,5-b]quinoxaline. However, MeSH and PhCH2SH ions attacked the sulfonate group of I (R = H) to form 3-hydroxyalloxazine. I (R = Me) reacted with MeOH, EtOH, PrOH, and to some degree Me2CHOH, in the presence of Et3N to furnish anhydro-1-hydroxy-3-methyl-4-(alkoxycarbonyl)-s-triazolo[4,3-a]quinoxalinium hydroxides. However, NaOMe in MeOH converted I (R = Me) to a mixture of anhydro-1-hydroxy-3-methyl-s-triazolo[4,3-a]quinoxalinium hydroxide (II) and 1-methyl-3-hydroxyflavazole. A saturated aqueous solution of Et3N transformed I (R = Me) to II, apparently via the corresponding unstable 4-carboxylic acid. Reactions of I (R = Me) with a number of aliphatic amines yielded either amides based on the above mesoionic system or on the 3-carboxamido-2-quinoxalyl semicarbazide structure. Reaction of I (R = Me) with KCN furnished 1-methylimidazolo[4,5-b]quinoxaline. Mechanisms to explain all of the degradations are advanced. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Related Products of 49679-45-0).
Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0) belongs to quinoxaline derivatives. Quinoxaline is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. Quinoxalines are used as dyes, pharmaceuticals, and antibiotics such as echinomycin, levomycin exhibiting antitumoral properties. Quinoxalines establish also the basis of anthelmintics and receptor antagonists.Related Products of 49679-45-0
Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider