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Access to dihydropyridinones and spirooxindoles: application of N-heterocyclic carbene-catalyzed [3+3] annulation of enals and oxindole-derived enals with 2-aminoacrylates

Author:
Zhao, Liang-Liang, Li, Xing-Shuo, Cao, Li-Li, Zhang, Rui, Shi, Xiao-Qian, Qi, Jing
Source:
Chemical communications 2017 v.53 no.44 pp. 5985-5988
ISSN:
1364-548X
Subject:
Lewis bases, chemical bonding, chemical reactions, heterocyclic nitrogen compounds
Abstract:
A strategy for the NHC-catalyzed synthesis of dihydropyridinones and spirooxindoles has been developed via [3+3] annulation reactions of enals or isatin-derived enals with 2-aminoacrylates under oxidative conditions. In this efficient strategy, the 2-aminoacrylates served as nucleophiles. Modifying the standard base switched the carbon–carbon double bond formation from 5,6-positions to 3,4-positions to generate 5,6-dihydropyridinones and 3,4-dihydropyridinones, respectively. Meanwhile, a diverse set of spirooxindole derivatives were also synthesized in good to excellent yields.
Agid:
6391576