Regioselective Synthesis of Pyranone-Fused Indazoles via Reductive Cyclization and Alkyne Insertion

Tz Yi Wu, Sandip Dhole, Manikandan Selvaraju, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

A novel and efficient method for the one-pot synthesis of 2H-indazole from readily available building blocks is reported. The reaction of 2-nitrobenzylamines with zinc and ammonium formate underwent partial reduction to nitroso-benzylamine followed by an intramolecular cyclization to afford 2H-indazole via N-N bond formation. The carboxylic acid moiety of indazole was proceeded to regioselective alkyne insertion under ruthenium catalysis to form pyranone-fused indazoles. The regioselectivity is influenced by the weak coordination of indazole ring nitrogen to the metal center.

Original languageEnglish
Pages (from-to)156-163
Number of pages8
JournalACS Combinatorial Science
Volume20
Issue number3
DOIs
StatePublished - 12 Mar 2018

Keywords

  • alkyne
  • indazoles
  • one-pot synthesis
  • reductive cyclization
  • regioselective synthesis

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