Photoenolization: Application to Synthesis of Indanone-Derived Biologically Interesting Compounds via o-Methylphenacyl Epoxides

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F10%3A00044541" target="_blank" >RIV/00216224:14310/10:00044541 - isvavai.cz</a>

Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Photoenolization: Application to Synthesis of Indanone-Derived Biologically Interesting Compounds via o-Methylphenacyl Epoxides

Popis výsledku v původním jazyce

Indan-1-one derivatives are important synthetic intermediates in organic, organometallic, or medicinal chemistry. For example, donepezil hydrochloride represents a new class of acetylcholinesterase inhibitors, which can interfere with the progression ofAlzheimer`s disease and is now one of the best-selling drugs worldwide. Here we present a new synthetic approach to indan-1-one derivatives. The key step is a photochemical enolization followed by cyclization and epoxide ring opening of substituted 1-(o-methylphenyl)-2,3-epoxypropan-1-one moiety. Mechanistic studies and quantum chemical calculations based on DFT and CASSCF level of theories will be shown to outline the reaction mechanism. The strategy will be discussed with respect to the synthesis of biologically interesting compounds, such as Indanocine.

Název v anglickém jazyce

Photoenolization: Application to Synthesis of Indanone-Derived Biologically Interesting Compounds via o-Methylphenacyl Epoxides

Popis výsledku anglicky

Indan-1-one derivatives are important synthetic intermediates in organic, organometallic, or medicinal chemistry. For example, donepezil hydrochloride represents a new class of acetylcholinesterase inhibitors, which can interfere with the progression ofAlzheimer`s disease and is now one of the best-selling drugs worldwide. Here we present a new synthetic approach to indan-1-one derivatives. The key step is a photochemical enolization followed by cyclization and epoxide ring opening of substituted 1-(o-methylphenyl)-2,3-epoxypropan-1-one moiety. Mechanistic studies and quantum chemical calculations based on DFT and CASSCF level of theories will be shown to outline the reaction mechanism. The strategy will be discussed with respect to the synthesis of biologically interesting compounds, such as Indanocine.

Druh

O - Ostatní výsledky

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/GA203%2F09%2F0748" target="_blank" >GA203/09/0748: Nové fotoaktivovatelné sloučeniny pro organickou chemii a biologii</a><br>

Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2010

Kód důvěrnosti údajů

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