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

Abstract

ZrOCl₂ · 8H₂O catalyzes the one-pot synthesis of β′-acetamido-β-dicarbonyl compounds in high yields from aldehyde, enolizable β-dicarbonyl compound, acetyl chloride, and acetonitrile in solvent as well as in solvent-free conditions. β′-Acetamido-β-ketoesters are formed in moderate to exclusive pref-diastereoselectivity.

Keywords:

• β′-Acetamido-β-dicarbonyls
• Lewis acid
• One-pot multicomponent synthesis
• ZrOCl₂ · 8H₂O

ACKNOWLEDGMENTS

The financial assistances from Council of Scientific and Industrial Research (CSIR), New Delhi (Scheme No. 01/1951/04/EMR-II) to R. G. and senior research fellowship to S. M. are gratefully acknowledged. The authors are also thankful to Fund for Improvement of Science and Technology Infrastructure-Department of Science and Technology (FIST-DST) (India) for supporting the Department of Chemistry, Jadavpur University, with NMR facilities.

Notes

^a Unoptimiszed chromatographed yields.

^b By ¹H-NMR.

^c Scaled-up experiment (∼ 10-fold).

^d With recovered ZrOCl₂ · 8H₂O (∼ 10-fold).

^e At 50°C.