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Synthesis 2019; 51(17): 3277-3286
DOI: 10.1055/s-0037-1611563
DOI: 10.1055/s-0037-1611563
paper
Manganese(III)-Based Oxidative Cyclization of N-Aryl-2-oxocycloalkane-1-carboxamides: Synthesis of Spiroindolinones
This research was supported by the Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (C) (No. 25410049 and 18K05109). We also acknowledge the Nissan Chemical Corporation for financial support.Weitere Informationen
Publikationsverlauf
Received: 22. März 2019
Accepted after revision: 04. Mai 2019
Publikationsdatum:
24. Mai 2019 (online)
This manuscript is dedicated to the late Professor Shô Ito, Professor Emeritus of Tohoku University, Japan, who showed Hiroshi Nishino the way as a chemist.
Abstract
The Mn(III)-based oxidative cyclization of twenty-five N-aryl-2-oxocycloalkane-1-carboxamides is investigated. The reactions progress efficiently to give the desired spiro[cycloalkane-1,3′-indoline]-2,2′-diones in high to quantitative yields. The easy conversion of the carbonyl functional group of one of the indoline products, 1′-methylspiro[cyclohexane-1,3′-indoline]-2,2′-dione, is also demonstrated.
Key words
spiro[cycloalkane-1,3′-indoline]-2,2′-diones - oxidative cyclization - 5-exo cyclization - radicals - heterocycles - spiro compounds - indolinonesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611563.
- Supporting Information
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