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 Full article

Journal

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

Output data

Year: 1993, Volume: 42, Number: 6, Pages: 1059-1062 Pages count : 4 DOI: 10.1007/BF00704199

Tags

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

Authors

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

Affiliations

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

Published print:

Jun 1, 1993

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