posted on 2023-12-14, 19:34authored byNikita Chakraborty, Bubul Das, Dinabandhu Barik, Kamal K. Rajbongshi, Bhisma K. Patel
A base (Et3N)-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 ΔELUMO–HOMO is calculated using Gaussian 16 at the B3LYP/6-31G(d,p)
level of theory.