HFIP-Promoted Friedel–Crafts Allenylation of Imidazopyridines with Propargyl Alcohols at Room Temperature

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 25, 2025

Herein, we report an efficient synthetic protocol for the Friedel–Crafts reaction of imidazo[1,2-a]pyridines with propargyl alcohols in HFIP. Notably, this FC allenylation works without any additional solvent or catalyst and requires neither inert conditions nor heating. In method, HFIP, besides offering hydrogen bonding alcohol, also stabilizes resultant carbocation, thus forming product. This method enables straightforward synthesis 1,3-enynes. The current offers a large substrate diversity good to excellent yields. We demonstrated gram-scale modifications.

Language: Английский

Strategic Methodologies for Efficient Synthesis of Imidazo[1,5-a]pyridine and Benzazepine Analogs via the Unique Ritter-Type Reaction

ACS Organic & Inorganic Au, Journal Year: 2024, Volume and Issue: 5(2), P. 117 - 135

Published: Dec. 17, 2024

We have developed novel approaches for synthesizing imidazo[1,5-a]pyridine and benzazepine analogs through a Ritter-type reaction. These methods utilize bismuth(III) trifluoromethanesulfonate (Bi(OTf)3), an efficient catalyst converting benzylic alcohol into cations, in combination with para-toluenesulfonic acid (p-TsOH·H2O). The procedures offer wide substrate scope deliver the desired products yields ranging from moderate to excellent.

Language: Английский