N-Oxide as an Intramolecular Oxidant in the Baeyer-Villiger Oxidation: Synthesis of 2-Alkyl-2H-indazol-3-yl Benzoates and 2-Alkyl-1,2-dihydro-3H-indazol-3-ones

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F16%3A33160844" target="_blank" >RIV/61989592:15310/16:33160844 - isvavai.cz</a>
Result on the web
<a href="http://pubs.acs.org/doi/ipdf/10.1021/acs.joc.6b00251" target="_blank" >http://pubs.acs.org/doi/ipdf/10.1021/acs.joc.6b00251</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.6b00251" target="_blank" >10.1021/acs.joc.6b00251</a>

Result language
angličtina
Original language name
N-Oxide as an Intramolecular Oxidant in the Baeyer-Villiger Oxidation: Synthesis of 2-Alkyl-2H-indazol-3-yl Benzoates and 2-Alkyl-1,2-dihydro-3H-indazol-3-ones
Original language description
In this study, we describe the intramolecular BaeyerMINUS SIGN Villiger oxidation of ketones to esters using N-oxide. 2-Nitro-N-alkyl-N-(2-oxo-2-phenylethyl)benzenesulfonamide compounds are known to ndergo base-mediated C-arylation followed by NMINUS SIGN N bond formation, producing unstable five-membered ring intermediates that spontaneously dehydrate to indazole oxides. We identified the reaction conditions under which the cyclic intermediate undergoes acid-mediated intramolecular BaeyerMINUS SIGN Villiger oxidation of the ketone in which N-oxide serves as the intramolecular oxidizing agent. The solid-phase synthesis plays a critical role in the successful transformation, allowing rapid access to the unstable but BaeyerMINUS SIGN Villiger oxidation-prone intermediate. This synthetic route provides practical access to 2-alkyl-2H-indazol-3-yl benzoates and 2-alkyl-1,2-dihydro-3H-indazol-3-ones, which are known privileged structures possessing remarkable diverse pharmacologically relevant activities.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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