Copper-Catalyzed One-Pot Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles from Arylacetic Acids and Hydrazides via Dual Oxidation.

Autor: Lekkala C; Department of Organic Chemistry & FDW, Andhra University, Visakhapatnam 530003, India., Bodala V; Department of Organic Chemistry & FDW, Andhra University, Visakhapatnam 530003, India., Yettula K; Department of Organic Chemistry & FDW, Andhra University, Visakhapatnam 530003, India., Karasala BK; Department of Organic Chemistry & FDW, Andhra University, Visakhapatnam 530003, India., Podugu RL; Department of Organic Chemistry & FDW, Andhra University, Visakhapatnam 530003, India., Vidavalur S; Department of Organic Chemistry & FDW, Andhra University, Visakhapatnam 530003, India.
Jazyk: angličtina
Zdroj: ACS omega [ACS Omega] 2022 Jul 27; Vol. 7 (31), pp. 27157-27163. Date of Electronic Publication: 2022 Jul 27 (Print Publication: 2022).
DOI: 10.1021/acsomega.2c01586
Abstrakt: A simple and efficient protocol has been developed to access symmetrical and unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles from arylacetic acids and hydrazides via copper-catalyzed dual oxidation under an oxygen atmosphere. Oxidative decarboxylation of arylacetic acids and oxidative functionalization of the imine C-H bond are the key steps. This is the first example of the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles through dual oxidation in one-pot. Avoidance of the expensive ligand and high yield of the products are advantageous features of the developed method.
Competing Interests: The authors declare no competing financial interest.
(© 2022 The Authors. Published by American Chemical Society.)
Databáze: MEDLINE