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Organocatalytic Regioselective [3+2] Annulation of Morita-Baylis-Hillman Carbonates with Azonaphthalenes: An Efficient Access to 3-Spiropyrazole- 2-oxindoles

[ Vol. 7 , Issue. 2 ]

Author(s):

Yuyu Cheng, Zhongyue Lu and Pengfei Li*   Pages 134 - 139 ( 6 )

Abstract:


Background: A cheap and commercially available organocatalyst, 4-dimethylaminopyridine was successfully employed in the regioselective [3+2] cycloaddition of isatin-derived Morita-Baylis- Hillman carbonates with azonaphthalenes for the construction of 3-spiropyrazole-2-oxindoles in excellent yields under mild conditions.

Methods: In the presence of 4-dimethylaminopyridine with a loading of 10 mol%, a series of isatinderived Morita-Baylis-Hillman carbonates reacted smoothly with azonaphthalenes in dichloromethane at room temperature to furnish 3-spiropyrazole-2-oxindoles in 72-98% yield.

Results and Conclusion: In summary, we have developed reasonably cheap and commercially available 4-dimethylaminopyridine-mediated regioselective [3+2] annulations between isatin-derived Morita- Baylis-Hillman carbonates and azonaphthalenes for the construction of 3-spiropyrazole-2-oxindoles under mild conditions.

Keywords:

Annulation, azonaphthalenes, MBH carbonates, 4-dimethylaminopyridine, regioselective, spirooxindole.

Affiliation:

Department of Chemistry, Southern University of Science and Technology, Department of Chemistry, Southern University of Science and Technology, Department of Chemistry, Southern University of Science and Technology

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