Metal-Free Catalyzed Synthesis of Fluorescent Indolizine Derivatives

J Org Chem. 2021 Sep 17;86(18):12737-12744. doi: 10.1021/acs.joc.1c01292. Epub 2021 Aug 28.

Abstract

A mild and high efficient method to prepare indolizines by two-component reaction with the acid as the catalyst was developed. In this reaction, a new ring efficiently formed in one-step reaction. A wide range of substrates could be applied and the desired products were obtained in 8-95% yields under metal-free conditions. Different indolizine derivatives (compounds 3a-3n) were synthesized by general conditions and microwave irradiation conditions, and compound 3a gave the best results with an isolated yield of 95% and 82%, respectively. The structures of synthesized compounds were characterized by spectral analysis, and compound 3m was confirmed by single crystal X-ray analysis. UV-vis absorption and fluorescence properties of these compounds were correlated with substituent groups on indolizine rings.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Indolizines*
  • Molecular Structure
  • Pyrazoles*
  • Spectrometry, Fluorescence

Substances

  • Indolizines
  • Pyrazoles
  • indolizine