Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione

• Main Authors: Yan Sun, Jing Sun, Chao-Guo Yan
• Format: Article
• Language: English
• Published: Beilstein-Institut 2013-01-01
• Series: Beilstein Journal of Organic Chemistry
• Subjects: arylamine; cyclopentanedione; isatin; multicomponent reaction; spiro compound
• Online Access: https://doi.org/10.3762/bjoc.9.2

A fast and convenient protocol for the synthesis of novel spiro[dihydropyridine-oxindole] derivatives in satisfactory yields was developed by the three-component reactions of arylamine, isatin and cyclopentane-1,3-dione in acetic acid at room temperature. On the other hand the condensation of isatin with two equivalents of cyclopentane-1,3-dione gave 3,3-bis(2-hydroxy-5-oxo-cyclopent-1-enyl)oxindole in high yields. The reaction mechanism and substrate scope of this novel reaction is briefly discussed.