4.7 Article

Synthesis of Imidazo[1,2-a]pyridines via Near UV Light-InducedCyclization of Azirinylpyridinium Salts

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 9, Pages 6514-6519

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c00514

Keywords

-

Funding

  1. Russian Science Foundation [20-13-00044]
  2. Russian Science Foundation [20-13-00044] Funding Source: Russian Science Foundation

Ask authors/readers for more resources

An efficient one-pot synthesis method for imidazo[1,2-a]pyridines has been developed, which involves the construction of the bicyclic framework of imidazo[1,2-a]pyridines in two steps. The method can also be used for the synthesis of imidazo[2,1-a]isoquinolines. Stable tetrafluoroborates were obtained by converting the unstable (2H-azirin-2-yl)pyridinium/isoquinolinium bromides, which can be cyclized to imidazo[1,2-a]pyridines under UV irradiation in the presence of bromide ions.
An efficient one-pot synthesis of imidazo[1,2-a]pyridines from 2-bromoazirines and pyridines has beendeveloped. The construction of the bicyclic framework ofimidazo[1,2-a]pyridines occurs in two steps through the formationof (2H-azirin-2-yl)pyridinium bromides followed by dehydrobro-minative UV light-induced cyclization. The method can also beapplied for the synthesis of imidazo[2,1-a]isoquinolines. Unstablein solution, (2H-azirin-2-yl)pyridinium/isoquinolinium bromideswere quantitatively converted to stable tetrafluoroborates, whichcan be cyclized to imidazo[1,2-a]pyridines under UV irradiation in the presence of bromide ions

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.7
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

No Data Available
No Data Available