Reaction of Isatin and 2-Chloropyridinium Salt: An Efficient and Diastereoselective Synthesis of α,β-Unsaturated Oxindoles.

Autor: Imani K; Department of Organic Chemistry, Shahid Beheshti University, Tehran 1983969411, Iran., Shirazi H; Department of Organic Chemistry, Shahid Beheshti University, Tehran 1983969411, Iran., Golchin G; Department of Organic Chemistry, Shahid Beheshti University, Tehran 1983969411, Iran., Bazgir A; Department of Organic Chemistry, Shahid Beheshti University, Tehran 1983969411, Iran.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2024 Oct 04; Vol. 89 (19), pp. 13937-13946. Date of Electronic Publication: 2024 Sep 22.
DOI: 10.1021/acs.joc.4c01069
Abstrakt: A new, mild, and diastereoselective method has been developed for the synthesis of β-pyridone-α,β-unsaturated oxindoles by the reaction of isatins and 2-chloropyridinium salts in EtOH at room temperature for 5 min. This method operates under mild reaction conditions, providing the product with a good yield and diastereoselectivity, and it exhibits excellent tolerance toward various functional groups. The predominant isomer is the Z isomer, which can convert to the E isomer in the presence of NaN 3 .
Databáze: MEDLINE