Redox-Neutral Three-Component Coupling of Phenacyl Azides, Aldehydes, and 1,3-Dicarbonyls to Access β-Enaminodiones
Lodsna Borkotoky1,2, Uma Devi Newar1,2, Bipul Sarma3
1Applied Organic Chemistry Group, Chemical Sciences and Technology Division, CSIR-North East Institute of Science and Technology (NEIST), Jorhat 785006, India.
Abstract:
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(1H)-one and dimedone.
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