2-Cyano-3-hydroxyimidazole 1-oxide

When treated with HNO3 in TFA, 2-cyano-3-hydroxyimidazole 1-oxide 310 (R1 = CN) is nitrated at the 4-position and the cyano group hydrolyzed, while the 2-carboxamido analogue 310 (R1 = CONH2) is dinitrated at the 4- and 5-position with simultaneous deoxygenation (1992ZOR2424). [Pg.55]

In a transformation which parallels those of azidopyrimidines (Section 4.08.2.3.1) 2-azidopyrazine 1-oxide (190) on thermolysis forms 2-cyano-l-hydroxyimidazole 2-azidopyrazines at 220 °C give 1-cyanoimidazoles via the nitrene intermediate (Scheme 110) (80H(14)1963). [Pg.495]

Aminopyrazine 1-oxide with aqueous nitrous acid followed by sodium azide gave 2-azidopyrazine 1 -oxide (57), which on heating with dry benzene at 85 gave 2-cyano-l-hydroxyimidazole (58) (1261, 1262). 3-Aminopyrazine 1-oxide p-toluenesulfonate fused with cyanoguanidine at 150-155 gave 3-(amidino-... [Pg.245]

Dihydropyrazine derivatives, on irradiation, give good yields of imidazoles.The thermolysis of 2-azidopyrazine 1-oxide gives 2-cyano-1 -hydroxyimidazole. ... [Pg.267]

Alkaline hydrolysis of 2-cyano-l-hydroxyimidazole 3-oxide affords the 2-carboxamide with barium hydroxide the corresponding carboxylic add salt is formed." Selective reaction at each of the two different cyano groups of 1,2-disubstituted 4,5-dicyanoimidazole allows the synthesis of purine derivatives of unequivocal structure. ... [Pg.321]

Alkaline hydrolysis of 2-cyano-l-hydroxyimidazole 3-oxide affords the... [Pg.321]

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