2008
Photochemical Synthesis of Substituted Indan-1-ones Related to Donepezil
POSPÍŠIL, Tomáš, Aneesh TAZHE VEETIL, Lovely ANGEL P. A a Petr KLÁNZákladní údaje
Originální název
Photochemical Synthesis of Substituted Indan-1-ones Related to Donepezil
Název česky
Fotochemická syntéza substituovaných indan-1-onů jako derivátů donepezilu
Autoři
POSPÍŠIL, Tomáš (203 Česká republika), Aneesh TAZHE VEETIL (356 Indie, domácí), Lovely ANGEL P. A (356 Indie, domácí) a Petr KLÁN (203 Česká republika, garant, domácí)
Vydání
Photochemical & Photobiological Sciences, Cambridge, UK, Royal Society of Chemistry, 2008, 1474-905X
Další údaje
Jazyk
angličtina
Typ výsledku
Článek v odborném periodiku
Obor
10401 Organic chemistry
Stát vydavatele
Velká Británie a Severní Irsko
Utajení
není předmětem státního či obchodního tajemství
Impakt faktor
Impact factor: 2.144
Kód RIV
RIV/00216224:14310/08:00026021
Organizační jednotka
Přírodovědecká fakulta
UT WoS
000255743700015
Klíčová slova anglicky
Photochemistry; donepezil; photoenolization
Štítky
Příznaky
Mezinárodní význam, Recenzováno
Změněno: 22. 3. 2011 14:03, prof. RNDr. Petr Klán, Ph.D.
V originále
A photoenolization reaction is shown to be the key reaction step in the preparation of substituted indan-1-ones as convenient precursors for the synthesis of donepezil, a well known acetylcholinesterase inhibitor. Model 2,5-dialkylphenacyl chlorides, differently substituted in the alpha carbon position, were found to produce indan-1-ones upon irradiation in non-nucleophilic solvents in high chemical yields via hydrogen chloride release. While direct excitation of 4,5-dimethoxy-2-methylphenacyl chloride led to a complex mixture of photoproducts, photolysis of the corresponding benzoate was found to form 5,6-dimethoxyindan-1-one in 62-72% chemical yields and a relatively low quantum efficiency (F = 0.02). This compound can then be easily converted to donepezil by standard synthetic steps described in the literature. Isotopic exchange and quenching experiments revealed that the product is obtained by the photoenolization process via the triplet excited state, while minor side-photoproducts originate from the singlet excited state. Irradiation of the reactant in neat acetone, used both as a triplet sensitizer and solvent at the same time, was found to form 5,6-dimethoxyindan-1-one exclusively in high (90%)chemical yield.
Česky
A photoenolization reaction is shown to be the key reaction step in the preparation of substituted indan-1-ones as convenient precursors for the synthesis of donepezil, a well known acetylcholinesterase inhibitor. Model 2,5-dialkylphenacyl chlorides, differently substituted in the alpha carbon position, were found to produce indan-1-ones upon irradiation in non-nucleophilic solvents in high chemical yields via hydrogen chloride release. While direct excitation of 4,5-dimethoxy-2-methylphenacyl chloride led to a complex mixture of photoproducts, photolysis of the corresponding benzoate was found to form 5,6-dimethoxyindan-1-one in 62-72% chemical yields and a relatively low quantum efficiency (F = 0.02). This compound can then be easily converted to donepezil by standard synthetic steps described in the literature. Isotopic exchange and quenching experiments revealed that the product is obtained by the photoenolization process via the triplet excited state, while minor side-photoproducts originate from the singlet excited state. Irradiation of the reactant in neat acetone, used both as a triplet sensitizer and solvent at the same time, was found to form 5,6-dimethoxyindan-1-one exclusively in high (90%)chemical yield.
Návaznosti
| GA203/05/0641, projekt VaV |
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| MSM0021622413, záměr |
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