SYNTHESIS OF 2-CHLOROPYRIMIDINES AND 4-CHLOROPYRIMIDINES WITH HYDROXPHENYL SUBSTITUENTS BY THE INTERACTION OF VILSMEIER-HAACK REAGENTS WITH (HYDROXYPHENYL)DIHYDROPYRIMIDIN-2-ONES AND (HYDROXYPHENYL)DIHYDROPYRIMIDIN-4-ONES

SYNTHESIS OF 2-CHLOROPYRIMIDINES AND 4-CHLOROPYRIMIDINES WITH HYDROXPHENYL SUBSTITUENTS BY THE INTERACTION OF VILSMEIER-HAACK REAGENTS WITH (HYDROXYPHENYL)DIHYDROPYRIMIDIN-2-ONES AND (HYDROXYPHENYL)DIHYDROPYRIMIDIN-4-ONES Научная публикация

Журнал

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

Вых. Данные

Год: 1993, Том: 42, Номер: 6, Страницы: 1059-1062 Страниц : 4 DOI: 10.1007/BF00704199

Ключевые слова

THIONYL CHLORIDE; PHOSPHORYL CHLORIDE; DIMETHYLFORMAMIDE; VILSMEIER-HAACK REAGENTS; DIHYDROPYRIMIDINONES; CHLOROPYRIMIDINES; PHENOLS; ARYL FORMATES; H-1 NMR

Авторы

Krivopalov V.P. ¹ , Nikolaenkova E.B. ¹

Организации

1	Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent'eva, 630090, Novosibirsk, Russian Federation

The reaction of 2- and 4-hydroxypyrimidines containing ortho- and para-hydroxyphenyl substituents with Vilsmeier-Haack reagents generated in situ from DMF and SOCl2 or POCl3 results in the chemoselective replacement of the heterocyclic hydroxyl group by chlorine and formylation of the phenolic hydroxyl group. Aryl formates are hydrolyzed under the conditions of their isolation to give the corresponding phenols, especially if the pyrimidyl fragment is ortho to the formyloxy group.

Krivopalov V.P. , Nikolaenkova E.B.
SYNTHESIS OF 2-CHLOROPYRIMIDINES AND 4-CHLOROPYRIMIDINES WITH HYDROXPHENYL SUBSTITUENTS BY THE INTERACTION OF VILSMEIER-HAACK REAGENTS WITH (HYDROXYPHENYL)DIHYDROPYRIMIDIN-2-ONES AND (HYDROXYPHENYL)DIHYDROPYRIMIDIN-4-ONES
Russian Chemical Bulletin. 1993. V.42. N6. P.1059-1062. DOI: 10.1007/BF00704199 WOS Scopus РИНЦ

Опубликована в печати:

1 июн. 1993 г.

Web of science	WOS:A1993NK88500021
Scopus	2-s2.0-33747890901
РИНЦ	30832393
OpenAlex	W1976809719