ZrOCl₂ · 8H₂O: An Efficient, Ecofriendly, and Recyclable Catalyst for Ultrasound-Accelerated, One-Pot, Solvent-Free Synthesis of 8-Aryl-7,8-dihydro-[1,3]dioxolo[4,5-g]quinolin-6-(5H)-one and 4-Aryl-3,4-dihydroquinolin-2(1 H)-one Derivatives

Abstract

A convenient, one-pot, solvent-free reaction of amines, aromatic aldehydes, and Meldrum's acid to form 8-aryl-7,8-dihydro-[1,3]dioxolo[4,5-g]quinolin-6-(5H)-one and 4-aryl-3,4-dihydroquinolin-2-(1H)-one in the presence of 10 mol% ZrOCl₂.8H₂O under ultrasonic irradiation is described. This new protocol offers several advantages including low catalyst loading, clean reaction, easy workup, use of recyclable and ecofriendly catalyst, short reaction times, good yields, and solvent-free conditions.

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GRAPHICAL ABSTRACT

Keywords:

• Amine
• 8-aryl-7,8-dihydro-[1,3]dioxolo[4,5-g]quinolin-6-(5H)-one
• 4-aryl-3,4-dihydroquinolin-2-(1H)-one
• catalyst
• Meldrum's acid
• ultrasound irradiation
• ZrOCl₂ · 8H₂O

ACKNOWLEDGMENT

We thank the Research Council of the University of Bu-Ali Sina for financial support to carry out this research.

Notes

^a 3,4-Methylendioxyaniline (0.137 g, 1 mmol), benzaldehyde (1 mmol), Meldrum's acid (0.15 g, 1 mmol), solvent (2 mL), ZrOCl₂ · 8H₂O (10 mol%).

^b Isolated yields.

^a 3,4-Methylendioxyaniline (0.137 g, 1 mmol), benzaldehyde (1 mmol), Meldrum's acid (0.15 g, 1 mmol), catalyst (10 mol%).

^b Isolated yields.

^a Aniline derivatives (1 mmol), benzaldehyde derivatives (1 mmol), Meldrum's acid (0.15 g, 1 mmol), solvent (2 mL), ZrOCl₂ · 8H₂O (10 mol%).

^b Isolated yields.