- Synthesis of novel 2-aminoimidazo[4,5-b]pyridines, including the thieno analogue of the cooked-food mutagen IFP
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Eight new compounds, including three new ring systems obtained via the Friedlunder condensation of ortto-aminothiophenecarbaldehydes 11, 21 and 24 with creatinine (8), are reported. The condensation afforded 1, which is the thieno analogue of the cooked-food mutagen IFP (2-amino-1,6-dimethylfuro[2,3-e] imidazo[4,5-b]pyridine), and the benzothieno[2,3-e]- and benzothieno[3,2-e] imidazo[4,5-b]pyridines 2 and 3. Attempts to condense 11 with isocreatinine (12) were unsuccesful. Desulfurization of 3 gave the known cooked-food carcinogen PhIP, The 2-nitro (4) and 2-hydroxy (5) derivatives of 3 are reported. The related 2-amino-1-methyl-imidazo[4,5-b]benzothiophene (25) was synthesized by a different route. Fully assigned 1H and 13C nmr data of all new compounds are reported.
- Bjoerk, Malin,Grivas, Spiros
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