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A convenient synthesis of linear pyridinoimidazo[1,2-a] pyridine and pyrroloimidazo[1,2-a] pyridine cores
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
2007 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 48, no 47, 8392-8395 p.Article in journal (Refereed) Published
Abstract [en]

Two new imidazo[1,2-a] pyridine derivatives, pyridinoimidazo[1,2-a] pyridine (10) and pyrroloimidazo[1,2-a] pyridine (16), were synthesised from 2-amino-4-methyl-5-nitropyridine (1) by linear cyclisation, making use of dimethylformamide dimethylacetal (DMFDMA) as an agent of vinylamine functionalisation. This report describes first the formation of pyridine and pyrroloimidazopyridine from (1), and then the formation of pyridine-fused and pyrrolo-fused pyridine by the Friedlander method and reductive cyclisation followed by treatment of the resulting adduct with chloroacetaldehyde.

Place, publisher, year, edition, pages
2007. Vol. 48, no 47, 8392-8395 p.
Keyword [en]
Friedländer reaction, Reductive cyclisation, DMFDMA, Pyridinoimidazo[1, 2-a]pyridine, Pyrroloimidazo[1, 2-a]pyridine
National Category
Pharmaceutical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-113040DOI: 10.1016/j.tetlet.2007.07.223ISI: 000252097200033OAI: oai:DiVA.org:uu-113040DiVA: diva2:289725
Available from: 2010-01-25 Created: 2010-01-25 Last updated: 2017-12-12Bibliographically approved

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