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Photochemical synthesis of substituted indan-1-ones related to donepezil

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Photochemical & Photobiological Sciences Vol - 7 Issue - 4

Photochemical & Photobiological Sciences Vol - 7 Issue - 3

Photochemical & Photobiological Sciences Vol - 7 Issue - 2

Photochemical & Photobiological Sciences Vol -6

Photochemical & Photobiological Sciences Vol -5

Photochemical & Photobiological Sciences Vol -4

Photochemical & Photobiological Sciences Vol -3

Photochemical & Photobiological Sciences Vol -2

Photochemical synthesis of substituted indan-1-ones related to donepezil

Content Provider	Royal Society of Chemistry (RSC)
Author	Veetil, Aneesh Tazhe Klán, Petr Pospíšil, Tomáš Antony, Lovely Angel Panamparambil
Copyright Year	2008
Abstract	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 α-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 (Φ ∼ 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.
Starting Page	625
Ending Page	632
Page Count	8
File Format	HTM / HTML PDF
ISSN	1474905X
Volume Number	7
Issue Number	5
Journal	Photochemical & Photobiological Sciences
DOI	10.1039/b719760h
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Benzoic acid Quantum Acetylcholinesterase inhibitor Donepezil Yield (chemistry) Alpha and beta carbon Irradiation Hydrogen chloride Photodissociation Solvent Pyrimidine dimer Acetone
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry

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The liquid hydrogen chloride solvent system. Part XIV. Reactions of π-cyclopentadienyldicarbonyliron dimer, of π-cyclopentadienylirondicarbonyl chloride, bromide, and iodide, and of π-cyclopentadienyltricarbonyliron chloride in the solvent

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Photochemical synthesis of substituted indan-1-ones related to donepezil

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