Реферат: Various methods of introducing deuterium into compounds containing serotonin (5-hydroxytryptamine, 5-HT) and dopamine (DA) were considered. By deuteration of 6,7-dihydroxy-5,8-dimethoxy-2H-chromen-2-one (1) and the reaction of its reduction product 6,7-dihydroxy-5,8-dimethoxychroman-2-one (2) with 5-HT and DA in dioxane and DMF, compounds 3a,b, which are deuterated analogues of 2,3-dimethoxy-5-methyl-p-benzoquinone containing moieties of biogenic amines, were obtained in yields of 25 and 20–30%, respectively. The technique of reduction of a double bond in compound 1 without the use of a solvent was worked out. This technique allows the reaction to be carried out at 100–200 °C, which results in an increase in the yield of the labeled product due to isotope exchange. The achieved yield of lactone 2 with the inclusion of 6–7 deuterium atoms was 60%. The benzyl protecting group was removed at 100 °C for 30 min in an atmosphere of gaseous deuterium. Deuterated compounds [D]3a and [D]3b contained 6–7 deuterium atoms in the quinone moiety. Condensation of [D]dopamine with lactone 2 gave compound 3b containing ∼2.5 atoms of deuterium. By deuteration of unlabeled 3a,b, isotopically labeled compounds containing 2.3 and 6.4 deuterium atoms were isolated in yields of 30 and 20%, respectively.

Библиографическая ссылка: Shevchenko V.P. , Nagaev I.Y. , Shevchenko K.V. , Andreeva L.A. , Myasoedov N.F. , Adaeva O.I. , Demchuk D.V. , Semenov V.V.
Introduction of deuterium into 2,3-dimethoxy-5-methyl-p-benzoquinone analogues containing serotonin and dopamine
Russian Chemical Bulletin. 2026. V.75. N2. P.653-660. DOI: 10.1007/s11172-026-4919-0 WOS Scopus OpenAlex

Даты:

Поступила в редакцию:	4 сент. 2024 г.
Опубликована online:	11 апр. 2026 г.

Идентификаторы БД:

≡ Web of science:	WOS:001738024100016
≡ Scopus:	2-s2.0-105036128254
≡ OpenAlex:	W7153598435

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