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

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

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 2009, Volume: 45, Number: 10, Pages: 1535-1540 Pages count : 6 DOI: 10.1134/S1070428009100200

Authors

Sedova V.F. ¹ , Krivopalov V.P. ¹ , Shkurko O.P. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Div, Novosibirsk 630090, Russia

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.

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

Published print:	Oct 1, 2009
Published online:	Nov 15, 2009

Web of science	WOS:000271810500020
Scopus	2-s2.0-70450217553
Elibrary	15308034
OpenAlex	W2066169479