Journal of the Chemical Society. Perkin transactions I p. 2253 - 2256 (1994)
Update date:2022-08-04
Topics:
Tzeng, Cherng-Chyi
Wei, Dau-Chang
Hwang, Long-Chih
Cheng, Ming-Chu
Wang, Yu
A number of 5-benzyl-5H-imidazo<4,5-e>-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.
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