The mechanism of oxidation of NADH analogues 5: Photooxidation of N-methyl substituted 1,4- and 1,2-dihydropyrimidines in the presence of quinones

The photoinduced interaction of the 1-methyl-4-phenyl-5-carbomethoxy-6-methyl-1,4(1,2)-dihydropyrimidines (1,4- and 1,2-DHPm) with quinones has been studied by means of CIDNP method in polar media. It was established that 1-methyl-4-phenyl-5-carboxymethyl-6-methylene-1,6-dihydropyrimidine (1,6-MDHPm...

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Bibliographic Details
Published in:Journal of photochemistry and photobiology. A, Chemistry. Chemistry., 2003-02, Vol.155 (1), p.119-126
Main Authors: Magin, I.M, Kruppa, A.I, Leshina, T.V, Lüsis, V, Muceniece, D
Format: Article
Language:English
Subjects:
CIDNP
Dihydropyrimidines
Photooxidation
Quinone
Radical ions
Radicals
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Summary:The photoinduced interaction of the 1-methyl-4-phenyl-5-carbomethoxy-6-methyl-1,4(1,2)-dihydropyrimidines (1,4- and 1,2-DHPm) with quinones has been studied by means of CIDNP method in polar media. It was established that 1-methyl-4-phenyl-5-carboxymethyl-6-methylene-1,6-dihydropyrimidine (1,6-MDHPm) is a main reaction product. It has been found that radical cation of DHPm is more reactive species than earlier studied radical cations of related N-methyl substituted dihydropyridines and is disposed to proton loss resulting in neutral pyrimidinyl radical. The 1,6-MDHPm was formed by hydrogen atom loss from 6-CH 3 group of pyrimidinyl radical. Oxidation of the pyrimidinyl radical to pyrimidinium cation was not detected. Formation of pyrimidinium cation was detected in the presence of a high concentration of acetic acid in the reaction mixture.
ISSN:1010-6030
1873-2666
DOI:10.1016/S1010-6030(02)00392-1