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Tautomeric structure of 1-methyldihydropyridazino-[3,4-b]quinoxalines in solution
Authors:Yoshihisa Kurasawa  Atsushi Takada  Ho Sik Kim  Yoshihisa Okamoto
Abstract:The reaction of 6-chloro-2-(1-methylhydrazino)quinoxaline 4-oxide 1 with ethyl 2-ethoxymethylene-2-cyano-acetate or ethoxymethylenemalononitrile gave 6-chloro-2-2-(2-cyano-2-ethoxycarbonylvinyl)-1-methylhy-drazino]quinoxaline 4-oxide 3a or 6-chloro-2-2-(2,2-dicyanovinyl)-1-methylhydrazino]quinoxaline 3b , respectively. The reaction of 3a with a base afforded 7-chloro-1-methyl-1,5-dihydropyridazino3,4-b]quinoxaline 4 . From the NOE spectral data, the 1-methyldihydropyridazino3,4-b]quinoxalines 2a, 2b and 4 were found to exist as the 1,5-dihydro form in a dimethyl sulfoxide or trifluoroacetic acid/dimethyl sulfoxide solution.
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