Synthesis of novel 2-aminoimidazo[4,5-b]pyridines, including the thieno analogue of the cooked-food mutagen IFP
2006 (English)In: Journal of Heterocyclic Chemistry, ISSN 0022-152X, Vol. 43, no 1, 101-109 p.Article in journal (Refereed) Published
Eight new compounds, including three new ring systems obtained via the Friedlander condensation of ortho-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 unsuccessful. 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 H-1 and C-13 nmr data of all new compounds are reported.
Place, publisher, year, edition, pages
2006. Vol. 43, no 1, 101-109 p.
IdentifiersURN: urn:nbn:se:sh:diva-14317DOI: 10.1002/jhet.5570430116ISI: 000234531100016ScopusID: 2-s2.0-30844448805OAI: oai:DiVA.org:sh-14317DiVA: diva2:468087