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Paper | Regular issue | Vol 65, No. 10, 2005, pp.2369-2380
Published online, 9th August, 2005
DOI: 10.3987/COM-05-10486
Synthesis of Thienoimidazo[4,5-b]pyridines and Thenylidenoimidazolinones

Malin Björk and Spiros Grivas*

*Unit for Organic Chemistry, Department of Biosciences, Karolinska Institutet, Södertörn University College, Novum Research Park, SE-141 57 Huddinge, Sweden


The two isomers 2-amino-1-methylimidazo[4,5-b]thieno[3,2-e]pyridine (3) and 2-amino-1-methylimidazo[4,5-b]thieno[2,3-e]pyridine (4) were synthesized by the Friedländer reaction starting from creatinine and the appropriate aminothiophenecarbaldehydes (11 and 13). Creatinine was also condensed with 2-nitro-3-thiophenecarbaldehyde (10) in ethylene glycol to yield the 2-amino-1-methyl-5-[2-(2-nitro-3-thenylidene)]-2-imidazolin-4-one (7a), with 3-amino-2-thiophenecarbaldehyde (13) under Perkin conditions to yield 2-acetamido-5-[2-(3-acetamido-2-thenylidene)]-1-methyl-2-imidazolin-4-one (8), and with 4-azido-3-thiophenecarbaldehyde (17) in acetic acid to yield 2-amino-5-[2-(4-azido-3-thenylidene)]-1-methyl-2-imidazolin-4-one (9). The thenylidenoimidazolinone (8) was converted into compound (4).