Photoenolization: Application to Synthesis of Indanone-Derived Biologically Interesting Compounds via o-Methylphenacyl Epoxides
The result's identifiers
Result code in 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>
Result on the web
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DOI - Digital Object Identifier
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Alternative languages
Result language
angličtina
Original language name
Photoenolization: Application to Synthesis of Indanone-Derived Biologically Interesting Compounds via o-Methylphenacyl Epoxides
Original language description
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.
Czech name
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Czech description
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Classification
Type
O - Miscellaneous
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
<a href="/en/project/GA203%2F09%2F0748" target="_blank" >GA203/09/0748: New photoactivatable compounds for organic chemistry and biology</a><br>
Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)
Others
Publication year
2010
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů