Three-component condensation of alpha-nitroacetophenone, aromatic aldehydes, and methylurea

Three-component condensation of alpha-nitroacetophenone, aromatic aldehydes, and methylurea Full article

Journal

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

Output data

Year: 2007, Volume: 56, Number: 6, Pages: 1184-1189 Pages count : 6 DOI: 10.1007/s11172-007-0180-3

Tags

3,4-dihydropyrimidin-2(1H)-ones; hexahydropyrimidin-2-ones; methylurea; aromatic aldehydes; alpha-nitroacetophenone; Biginelli reaction; retro-Henry reaction

Authors

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

Affiliations

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

The three-component condensation of aromatic aldehydes, methylurea, and alpha-nitro-acetophenone affords both N(1)- and N(3)-methyl-substituted 4,6-diaryl-5-nitro-3,4-dihydropyrimidin-2(1H)-ones depending on the structure of aldehyde. Intermediate 4,6-diaryl-4-hydroxy-3-methyl-5-nitrohexahydropyrimidin-2-ones and trisubstituted urea, which is the transformation product of the 4-hydroxy-3-methyl derivative in an acidic medium (retro-Henry reaction), were identified in the reaction mixtures.

Sedova V.F. , Krivopalov V.P. , Shkurko O.P.
Three-component condensation of alpha-nitroacetophenone, aromatic aldehydes, and methylurea
Russian Chemical Bulletin. 2007. V.56. N6. P.1184-1189. DOI: 10.1007/s11172-007-0180-3 WOS Scopus РИНЦ

Седова В.Ф. , Кривопалов В.П. , Шкурко О.П.
Особенность протекания трехкомпонентной конденсации α-нитроацетофенона, ароматических альдегидов и метилмочевины
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2007. №6. С.1141-1145. РИНЦ

Published print:

Jun 1, 2007

Web of science	WOS:000251971700015
Scopus	2-s2.0-36949026515
Elibrary	13538803
OpenAlex	W2950613045