Synthesis of Spiro[indoline-3,3′-pyridine]-2,2′-diones via an Annulo- and Diastereospecific [2 + 4] Annulation
Abstract
A tandem strategy has been designed and implemented for the efficient synthesis of spirooxindoles from 3-diazoquinoline-2,4-diones with α,β-unsaturated imines. The synthetic strategy involves the ring-contractive Wolff rearrangement of 3-diazoquinoline-2,4-diones, [2 + 4] annulation of α-oxoketenes with α,β-unsaturated imines, and transannulation, affording annulo- and diastereospecific spiro[indoline-3,3'-pyridine]-2,2'-diones in excellent yields.
Fields of Study & Subjects
Cyclopropane Reaction Mechanisms
Synthesis and Reactivity of Heterocycles
Synthesis and bioactivity of alkaloids
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 11
- Pages
- 3631–3636
- Publication date
- 6 March 2026
- Language
- EN