Synthesis of substituted 3,4-dihydropyrimidin-2(1H)-ones and pyrimidin-2(1H)-ones by the Biginelli reaction with 3,5-Di-tert-butyl-4-hydroxybenzaldehyde Full article
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Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393 |
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| Output data | Year: 2009, Volume: 45, Number: 10, Pages: 1535-1540 Pages count : 6 DOI: 10.1134/S1070428009100200 | ||
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Abstract:
Three-component acid-catalyzed cyclocondensation of 3,5-di-tret-butyl-4-hydroxybenzaldehyde with urea and ethyl acetoacetate or alpha-nitroacetophenone (Biginelli reaction) under homogeneous conditions gave the corresponding 5-substituted 3,4-dihydropyrimidin-2(1H)-ones having in position 4 of the heteroring an aryl substituent with sterically shielded hydroxy group. The condensation catalyzed by inorganic salts (Fe3+, Co2+, Zn2+, Li+) was successful only with ethyl acetoacetate as initial methylene-active component. Under analogous conditions, acetophenone and 4-fluoroacetophenone gave rise to 4,6-diarylpyrimidin-2(1H)-ones which are capable of undergoing phenol-quinonemethide tautomerism.
Cite:
Sedova V.F.
, Krivopalov V.P.
, Shkurko O.P.
Synthesis of substituted 3,4-dihydropyrimidin-2(1H)-ones and pyrimidin-2(1H)-ones by the Biginelli reaction with 3,5-Di-tert-butyl-4-hydroxybenzaldehyde
Russian Journal of Organic Chemistry. 2009. V.45. N10. P.1535-1540. DOI: 10.1134/S1070428009100200 WOS Scopus РИНЦ OpenAlex
Synthesis of substituted 3,4-dihydropyrimidin-2(1H)-ones and pyrimidin-2(1H)-ones by the Biginelli reaction with 3,5-Di-tert-butyl-4-hydroxybenzaldehyde
Russian Journal of Organic Chemistry. 2009. V.45. N10. P.1535-1540. DOI: 10.1134/S1070428009100200 WOS Scopus РИНЦ OpenAlex
Dates:
| Published print: | Oct 1, 2009 |
| Published online: | Nov 15, 2009 |
Identifiers:
| Web of science: | WOS:000271810500020 |
| Scopus: | 2-s2.0-70450217553 |
| Elibrary: | 15308034 |
| OpenAlex: | W2066169479 |