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Sequential Multicomponent Synthesis of 2-(Imidazo[1,5-alpha]pyridin-1-yl)-1,3,4-Oxadiazoles

Kurhade, S., Konstantinidou, M., Sutanto, F., Kurpiewska, K., Kalinowska-Tluscik, J. & Domling, A., 14-Mar-2019, In : European Journal of Organic Chemistry. 2019, 10, p. 2029-2034 6 p.

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DOI

A 21 membered library of 2-(imidazo[1,5-alpha]pyridine-1-yl)-1,3,4-oxadiazoles is synthesized in an unprecedented short sequence starting from an Ugi tetrazole reaction with a cleavable isocyanide component. The intermediate tetrazole is subjected to an acetic anhydride-mediated cyclization, followed by a Huisgen-type rearrangement with acyl chlorides to afford the imidazopyridine-oxadiazole bis-heterocycles. The scope and limitations of the methodology were investigated with substitutions on both the oxadiazole and the imidazopyridine rings. The introduced enabling technology for imidazopyridine oxadiazole synthesis combines a short reaction sequence with high scaffold diversity, based on commercially available starting materials and high functional groups tolerance.

Original languageEnglish
Pages (from-to)2029-2034
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number10
Publication statusPublished - 14-Mar-2019

    Keywords

  • MCR chemistry, Oxadiazoles, Huisgen rearrangement, Tetrazoles, Imidazopyridines, SPECTRAL-LUMINESCENT PROPERTIES, 1,3,4-OXADIAZOLE DERIVATIVES, TETRAZOLES, ACYLATION

ID: 118610845