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
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Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171 |
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| 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 | ||
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Abstract:
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.
Cite:
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 OpenAlex
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 OpenAlex
Dates:
| Published print: | Jun 1, 1993 |
Identifiers:
| Web of science: | WOS:A1993NK88500021 |
| Scopus: | 2-s2.0-33747890901 |
| Elibrary: | 30832393 |
| OpenAlex: | W1976809719 |