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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2016

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Organic Chemistry

ISSN

0022-3263

e-ISSN

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Svazek periodika

81

Číslo periodika v rámci svazku

9

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

12

Strana od-do

3585-3596

Kód UT WoS článku

000375890100014

EID výsledku v databázi Scopus

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