Synthesis of New Iminocoumarins Bearing Parabanic Moieties

Abstract

The synthesis of novel substituted 3-p-nitro-phenyliminocoumarins and corresponding N-ureaiminocoumarins is described. The condensation of these materials with oxalyl chloride leads to the corresponding N-parabanic iminocoumarins, which have not previously been described, in moderate or good yields and high selectivity. The structures were characterized by Fourier transform infrared, ¹H and ¹³C NMR, and elemental analysis.

Keywords:

• N-Hydrazonochromene
• iminocoumarin
• Knoevenagel condensation
• Schmidt reaction

ACKNOWLEDGMENTS

The authors acknowledge the Ministry of Higher Education, Scientific Research, and Technology in Tunisia for their financial support. They also thank Pr. Rachid El Gharbi for his useful discussions about this work.

Notes

^a Yields obtained with piperidine as catalyst.