Base-Promoted Synthesis of <i>S</i>-Arylisothiazolones via Intramolecular Dehydrative Cyclization of α-Keto-<i>N</i>-acylsulfoximines
Nikita Chakraborty, Bubul Das, Dinabandhu Barik, Kamal Krishna Rajbongshi, Bhisma K. Patel
Abstract
A base (Et 3 N)-promoted synthesis of 1,4-diarylisothiazolones from α-keto- N -acylsulfoximines has been achieved. The reaction proceeds via α-hydrogen abstraction from sulfoximine, followed by an intramolecular nucleophilic attack at the keto carbonyl to form a tert -hydroxy isothiazolone intermediate. The 1,4-substituted isothiazolone is obtained after dehydration via an E1cB path. This one-pot synthesis of isothiazolinones has a broad substrate scope, has a high atom economy, and provides products with good yields. The Δ E LUMO–HOMO is calculated using Gaussian 16 at the B3LYP/6-31G(d,p) level of theory.
Topics & Concepts
ChemistryIntramolecular forceNucleophileMedicinal chemistryHydrogen atom abstractionImineStereochemistrySubstrate (aquarium)Combinatorial chemistryHydrogenOrganic chemistryCatalysisGeologyOceanographySynthesis and Catalytic ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods