SOCl 2 -Catalyzed Meyer-Schuster Rearrangement of 3°-Propargylic Alcohols: Synthesis of Densely Arene-Substituted Pyrazolines Bearing Quaternary Centers from α,β-Unsaturated Carbonyl Compounds and Arylhydrazines.

Autor: Jat RS; School of Chemical Sciences and Pharmacy, Central University of Rajasthan, Ajmer, Rajasthan 305817, India., Bhanuchandra M; School of Chemical Sciences and Pharmacy, Central University of Rajasthan, Ajmer, Rajasthan 305817, India.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2023 Sep 15; Vol. 88 (18), pp. 13184-13190. Date of Electronic Publication: 2023 Sep 05.
DOI: 10.1021/acs.joc.3c01387
Abstrakt: Meyer-Schuster rearrangement of 3°-propargyl alcohol to the corresponding α,β-unsaturated carbonyl compounds under SOCl 2 catalysis has been reported. Terminal and internal propargyl alcohols efficiently participated in the reaction. Furthermore, we have demonstrated the synthetic utility of conjugated carbonyl compounds to access densely arene-substituted pyrazolines bearing quaternary centers by reacting with arylhydrazine hydrochloride. Isotopic labeling studies were carried out to gain insights into the reaction mechanism.
Databáze: MEDLINE