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Synthesis 2022; 54(10): 2423-2432
DOI: 10.1055/a-1731-2703
DOI: 10.1055/a-1731-2703
paper
N-Iodosuccinimide-Promoted Selective Construction of Cyclopropyl and Dihydrofuranyl Spirooxindoles from Alkylidene Oxindoles and Annular β-Dicarbonyl Compounds
This work was supported by the Natural Science Foundation of Anhui Province (2008085QB64), Foundation of Anhui Province Key Laboratory of Clean Energy Materials and Chemistry for Sustainable Conversion of Natural Resources (LCECSC-15), Pre-research Project of National Natural Science Foundation of Anhui Polytechnic University (Xjky2020079, 2019yyzr09), Foundation of China Tobacco Anhui Industrial Corporation (2020146) and Foundation of China National Tobacco Corporation (11201903003).
Abstract
An efficient N-iodosuccinimide-promoted cyclization of readily available alkylidene oxindoles with annular β-dicarbonyl compounds has been demonstrated. With five-membered cyclic β-dicarbonyl compounds as the starting materials, a series of cyclopropyl oxindoles can be obtained in good to excellent yields, whereas the method affords dihydrofuranyl spirooxindoles almost quantitatively when six- or seven-membered cyclic β-dicarbonyl compounds are employed. This protocol provides a new alternative to the practical synthesis of structurally diverse spirooxindoles.
Key words
spirooxindoles - N-iodosuccinimide - β-dicarbonyl compounds - selective synthesis - cyclizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1731-2703.
- Supporting Information
Publication History
Received: 18 November 2021
Accepted after revision: 04 January 2022
Accepted Manuscript online:
04 January 2022
Article published online:
21 February 2022
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For reviews on the synthesis of spirooxindoles, see:
For selected examples on the synthesis of cyclopropyl spirooxindoles, see:
For selected examples on the synthesis of dihydrofuranyl spirooxindoles, see:
For selected examples, see:
For selected examples, see: