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

Santosh Kurhade, Markella Konstantinidou, Fandi Sutanto, Katarzyna Kurpiewska, Justyna Kalinowska-Tluscik, Alexander Domling*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

4 Citations (Scopus)
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Abstract

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
DOIs
Publication statusPublished - 14-Mar-2019

Keywords

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

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