159554-19-5Relevant academic research and scientific papers
Condensed 1,2,4-Triazines: Synthesis of 5-Benzyl-5H-imidazo-1,2,4-triazine 1-Oxides (9-Benzyl-6-azapurine 6-Oxides)
Tzeng, Cherng-Chyi,Wei, Dau-Chang,Hwang, Long-Chih,Cheng, Ming-Chu,Wang, Yu
, p. 2253 - 2256 (2007/10/02)
A number of 5-benzyl-5H-imidazo-1,2,4-triazine 1-oxides, bioisosteric isomers of antiviral 9-benzylpurines, have been prepared.Oxidation of 6-amino-5-benzylamino-3-methylsulfanyl-1,2,4-triazine 1, with excess of m-chloroperbenzoic acid afforded 6-amino-5-benzylamino-3-methylsulfonyl-1,2,4-triazine 1-oxide 2 in 75percent yield.The 3-methylsulfonyl group, which is a good leaving group, has been replaced with various nucleophiles to give 3-amino 4, 3-methoxy 5 and 3-hydrazino 8 derivatives.Oxidative dehydrazination of 8 with mercury(II) oxide (HgO) in ethanol gave 6-amino-5-benzylamino-1,2,4-triazine 1 oxide 9 in a moderate yield.The 1,2,4-triazine 1-oxides were then cyclized with triethyl orthoformate (TEOF) to afford the title compounds in 28-88percent yields.
