Multicomponent Reaction Based Synthesis of 1-Tetrazolylimidazo[1,5- a]pyridines

Santosh Kurhade, Elmar Diekstra, Fandi Sutanto, Katarzyna Kurpiewska, Justyna Kalinowska-Tłuścik, Alexander Dömling

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Abstract

A series of unprecedented tetrazole-linked imidazo[1,5- a]pyridines are synthesized from simple and readily available building blocks. The reaction sequence involves an azido-Ugi-deprotection reaction followed by an acetic anhydride-mediated N-acylation-cyclization process to afford the target heterocycle. Furthermore, the scope of the methodology was extended to diverse R3-substitutions by employing commercial anhydrides, acid chlorides, and acids as an acyl component. The scope for the postmodification reactions are explored and the usefulness of the synthesis is exemplified by an improved three-step synthesis of a guanylate cyclase stimulator.
Original languageEnglish
Pages (from-to)3871-3874
Number of pages4
JournalOrganic letters
Volume20
Issue number13
DOIs
Publication statusPublished - 6-Jul-2018

Keywords

  • acid anhydride
  • pyridine derivative
  • acylation
  • chemical structure
  • cyclization
  • synthesis

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