Trifluoroacetic Acid as an Effective Catalyst for Biginelli Reaction: One‐Pot, Three‐Component Synthesis of 3,4‐Dihydropyrimidin‐2(1H)‐ones (and‐Thiones)

Abstract

Trifluoroacetic acid (TFA) is introduced as an effective catalyst for promotion of Biginelli reaction. 3,4-Dihydropyrimidin-2(1H)-one (-thione) derivatives (DHPMs) were simply and efficiently prepared using TFA catalyzed one-pot, three-component condensationβ-dicarbonyl compounds, aldehydes and urea (thio).

Synthesis, Redox Properties and Antibacterial Activity of Hindered Phenols Linked to Heterocycles

“…The most common catalysts reported for the Biginelli reaction are mineral acids (H 2 SO 4 [44], HCl [45], TFA [46]), Lewis acids (CoCl 2 , ZnCl 2 [47]), and other catalytic systems: FeCl 3 + HCl [48], TMSCl + NaI [49]. However, in our hands, the products were not obtained when all these conditions were employed.…”

“…To expand the range of pyrimidine derivatives, a number of 3,4-dihydropyrimidine (thiones)ones with a hindered phenol fragment were obtained by Biginelli reaction, according to Scheme 3. The most common catalysts reported for the Biginelli reaction are mineral acids (H2SO4 [44], HCl [45], TFA [46]), Lewis acids (CoCl2, ZnCl2 [47]), and other catalytic systems: FeCl3 + HCl [48], TMSCl + NaI [49]. However, in our hands, the products were not obtained when all these conditions were employed.…”

Synthesis of some New Fused Pyrimidine Compounds

“…Biginelli reaction is an efficient one-pot multicomponent condensation reaction that is used widely in organic and medical chemistry (Bose et al, 2005;Kulkarn et al, 2009;Mochaddas et al, 2012). Starting from aldehyde, Urea(thiourea) and β-keto ester under strongly acidic condition represented by Lewis acid to obtaine the pyrimidine-2-one analogs (Kappe, 1993;Mohammadizadeh and Firoozi, 2011), which received a significant attention owing to their biological (Shutalev et al, 1998;Mobinikhaledi and Kalhor, 2010) and pharmaceutical properties (Phucho et al, 2009;Piqani and Zhang, 2011;Shaikh et al, 2012) such as antihypertensive (Atwal et al, 1989;Atwal et al, 1990), antiinflammatory and antibacterial (Jadhav et al, 2012;Badadhe et al, 2011, Akbas et al, 2010 and antimicrobial (Beena and Akelesh, 2012) were also studied depending on this type of synthesis.…”

Effect of the Exchanged Cation in an Algerian Montmorillonite Used as a Heterogeneous Catalyst for Biginelli Reaction

“…These latter are well known to have important therapeutic and pharmaceutical properties; indeed they work as tension regulators and calcium blockers, [11][12][13] moreover they show anti-HIV, 14 anti-malarial, 15 anti-epileptics, 16 antitumors, [17][18][19][20] anti-microbials, 21 anti-inflammatories, 22 anti-tubercular, [23][24] anti-bacterials, [25][26] and analgesic activities. 27 Given its importance, the Biginelli reaction has been the subject of several researches and was carried out in the presence of various catalysts such as Brønsted acids in homogeneous medium as HCl, [28][29][30][31][32] H 2 SO 4, [33][34] para-toluenesulfonic acid, 35 methanesulfonic acid, 36 HBF 4 , 37 b oric acid, 38 phenylboronic acid, 39 formylphenylboronic acid, 40 carboxylic acid, 41 molybdophosphoric acid, 42 trifluoroacetic acid, 43 Lewis acids in homogeneous medium [44][45][46][47] as FeCl 2 , FeCl 3 , NiCl 2 , CoCl 2 , Ce(NO 3 ) 3 , and heterogeneous catalysts as Fe 2 O 3 nanoparticles, 48 Nafion-Ga, Al 2 O 3 , TiO 2 , SiO 2 oxides. [49][50] The Biginelli reaction was also carried out in the presence of montmorillonite of different origins, which has undergone various modifications and treatments.…”