N‑Heterocyclic Carbene-Catalyzed
Facile Synthesis of Phthalidyl Sulfonohydrazones: Density Functional
Theory Mechanistic Insights and Docking Interactions
posted on 2024-02-27, 05:03authored byTanmoy Ghosh, Debabrata Barman, Krishanu Show, Rabindranath Lo, Debashree Manna, Tapas Ghosh, Dilip K. Maiti
N-heterocyclic carbene catalysis reaction
protocol
is disclosed for the synthesis of phthalidyl sulfonohydrazones. A
broad range of N-tosyl hydrazones react effectively
with phthalaldehyde derivatives under open-air conditions, enabling
the formation of a new C–N bond via an oxidative path. The
reaction proceeds under mild reaction conditions with broad substrate
scopes, wide functional group tolerance, and good to excellent yields.
The mechanistic pathway is studied successfully using control experiments,
competitive reactions, ESI-MS spectral analyses of the reaction mixture,
and computational study by density functional theory. The potential
use of one of the phthalidyl sulfonohydrazone derivatives as the inhibitor
of β-ketoacyl acyl carrier protein synthase I of Escherichia coli is investigated using molecular
docking.