Redox-Neutral Three-Component Coupling of Phenacyl Azides, Aldehydes, and 1,3-Dicarbonyls to Access β-Enaminodiones.

Autor: Borkotoky L; Applied Organic Chemistry Group, Chemical Sciences and Technology Division, CSIR-North East Institute of Science and Technology (NEIST), Jorhat 785006, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, Uttar Pradesh 201002, India., Newar UD; Applied Organic Chemistry Group, Chemical Sciences and Technology Division, CSIR-North East Institute of Science and Technology (NEIST), Jorhat 785006, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, Uttar Pradesh 201002, India., Sarma B; Department of Chemical Sciences, Tezpur University, Tezpur 784028, India., Maurya RA; Applied Organic Chemistry Group, Chemical Sciences and Technology Division, CSIR-North East Institute of Science and Technology (NEIST), Jorhat 785006, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, Uttar Pradesh 201002, India.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2023 May 05; Vol. 88 (9), pp. 5329-5340. Date of Electronic Publication: 2023 Apr 20.
DOI: 10.1021/acs.joc.2c02847
Abstrakt: Heating an equimolar mixture of phenacyl azides, aldehydes, and cyclic 1,3-dicarbonyls to 100 °C without any solvent, catalyst, or additive led to efficient three-component redox-neutral coupling to yield β-enaminodiones in high yields (75-86%). The scope of the synthetic method that gives dinitrogen and water as the only byproducts was successfully demonstrated by synthesizing 34 structurally diverse β-enaminodiones by taking differentially substituted phenacyl azides, aldehydes and 4-hydroxycoumarins, and 4-hydroxy-1-methylquinolin-2(1 H )-one and dimedone.
Databáze: MEDLINE