Synthesis of novel acridines, tetrahydrodipyrazolo [3,4-b:4',3'-e]pyridines, tri-substituted methanes (TRSMs) bearing 2-(4-(1-phenyl-1H-pyrazol-3-yl)phenoxy)-N-phenylacetamide unit as novel hybrid molecules

Abstract

In this study novel 2-(4-(1-phenyl-1H-pyrazol-3-yl)phenoxy)-N-arylacetamide hybrids with fused 1,4-dihydropyridines such as acridines and tetrahydrodipyrazolo[3,4-b:4',3'-e]pyridines were successfully and efficiently prepared through a one-pot multi-component reaction of 2-(4-(4-formyl-1-phenyl-1H-pyrazol-3-yl)phenoxy)-N-arylacetamide with dimedone, or 5-methyl-2,4-dihydro-3H-pyrazol-3-one at reflux. The tri-substituted methanes (TRSMs) were synthesized through the reaction of the appropriate aldehyde with 6-aminothiouracil and 4-hydroxycoumarin. The structures of novel compounds were confirmed based on spectral data.

GRAPHICAL ABSTRACT

Keywords:

• 2-(4-(4-Formyl-1-phenyl-1H-pyrazol-3-yl)phenoxy)-N-arylacetamide
• dimedone
• 5-methyl-2,4-dihydro-3H-pyrazol-3-one
• 4-hydroxycoumarin
• fused 1,4-dihydropyridines
• tri-substituted methanes (TRSMs)

Acknowledgements

Amr M. Abdelmoniem, Ismail A. Abdelhamid, and Ahmed H. M. Elwahy acknowledge the Alexander von Humboldt Foundation for a Georg Forster and an Alexander von Humboldt research fellowship, respectively. The authors are very thankful to Prof. Dr. Holger Butenschön, Institut für Organische Chemie, Leibniz Universität Hannover, for kind hospitality and useful discussion.