ZrOCl₂•8H₂O-Catalyzed One-Pot Multicomponent Synthesis of β′-Acetamido-β-dicarbonyl Compounds with Special Reference to pref-Selective β′-Acetamido-β-ketoesters

Abstract

ZrOCl 2 Á8H 2 O catalyzes the one-pot synthesis of b 0 -acetamido-bdicarbonyl compounds in high yields from aldehyde, enolizable b-dicarbonyl compound, acetyl chloride, and acetonitrile in solvent as well as in solvent-free conditions. b 0 -Acetamido-b-ketoesters are formed in moderate to exclusive prefdiastereoselectivity.

ZrOCl2·8H2O: a highly efficient catalyst for the synthesis of 1,8‐dioxo‐octahydroxanthene derivatives under solvent‐free conditions

“…The system also worked well for α,β-unsaturated aldehydes to afford the product in 90% yield (Table 2, entry 34). The acid-sensitive heterocyclic aldehydes such as thiophene-2-carbaldehyde, pyridine-2-carbaldehyde, pyridine-3-carbaldehyde and pyridine-4-carbaldehyde (Table 2, entries [35][36][37][38] were also tested and the corresponding xanthene derivatives were obtained in high yields. We also scaled up the reaction of 4-chlorobenzaldehyde (1j) by 10-fold without any significant decrease in the product yield (94% yield).…”