[CH3:1][O:2][C:3]([C:5]1[Se:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[C:7]([N+:14]([O-])=O)[CH:6]=1)=[O:4].COC(C1[Se]C(C(OC)=O)=CC=1[NH2:26])=O.N([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+].[CH3:41][NH:42][CH3:43]>[Fe]>[CH3:41][N:42]([N:26]=[N:14][C:7]1[CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[Se:9][C:8]=1[C:10]([O:12][CH3:13])=[O:11])[CH3:43]
Oxidation of methyl 5-methylselenophene-2-carboxylate with selenium dioxide provided methyl 5-formylselenophene-2-carboxylate, which on further oxidation with silver nitrate gave selenophene-2,5-dicarboxylic acid. Nitration of selenophene-2,5-dicarboxylic acid and esterfication provided methyl 5-(methoxycarbonyl)-3-nitroselenophene-2-carboxylate in good yield. The nitro functionality is reduced to amines using suitable reducing agents, for example, iron powder or any other nitro reducing agents in good yield. Diazotization of methyl-amino-5-(methoxycarbonyl)selenophene-2-carboxylate with sodium nitrite followed by treatment with potassium carbonate/dimethylamine provides methyl 3-[(dimethylamino)diazenyl]-5-(methoxycarbonyl)selenophene-2-carboxylate. Treatment of the ester with ammonia gave the required 3-[(dimethylamino)diazenyl]selenophene-2,5-dicarboxamide (compound 2).
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