Biginelli reaction for synthesis of novel trifluoromethyl derivatives of bis(tetrahydropyrimidinone)benzenes

Acid Catalyzed One‐pot Three‐component Biginelli‐type Synthesis of Some New Symmetrical Bis 3,4‐dihydropyrimidin‐2(1H)‐ones/thiones

“…However, so far, the synthesis of mono 3,4‐dihydropyrimidones has been taken into considerable interest while the synthesis of Biginelli compounds, containing two dihydropyrimidinone units, have been less studied and reported. We have found few publications in which the use of bis reagents, that is, these have two similar functional groups necessary for the Biginelli reaction has been described . Improved conditions have been found to carry out the Biginelli reaction for the synthesis of bis dihydropyrimidones 1 and 2 in very good yields.…”

“…An effective one‐pot synthesis of bis dihyrodpyrimidines 3 using TMSCl through Biginelli condensation reaction of terephthalic aldehyde, 1,3‐dicarbonyl compounds and urea (thiourea) or quanidine under MW irradiation was reported (Fig. ) . Benzene bridged bis dihydropyrimidinones 4 were performed with compounds having two β‐keto ester moieties (for building up two pyrimidine rings) in a single molecule (Fig.…”

The first application of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones in a three-component condensation protocol for the synthesis of 3-acyl-4-aryl-2-(trifluoromethyl)-2-hydroxy-3,4,7,8-tetrahydro-2H-chromen-5(6H)-ones

“…The development of multicomponent reactions (MCRs) is nowadays of great importance in synthetic organic chemistry, since they offer one-pot combinations of two or more components in one step, allowing the formation of molecules with more complex structures [1]. In addition, the design of MCRs to produce elaborate active compounds has become an important area of research in combinatorial and medicinal chemistry [2].…”

Preparation of pyrimidine derivatives through three-component reactions of dialkyl (2-oxo-3,3,3-trifluoropropyl)phosphonates

“…stirring in acetonitrile at room temperature with a catalytic amount of trimethylchlorosilane [11,12]. As in the examples of the Biginelli reaction of -dicarbonyl compounds with fluoroalkyl groups [12][13][14][15][16], the cyclization products of the oxophosphonate 1a are the 4-hydroxytetrahydropyrimidin-2-ones (2a-c) but dehydratation and formation of classical 3,4-dihydropyrimidin-2-one Biginelli reaction products are not observed. The tetrahydropyrimidin-2-ones 2a-c contain three asymmetric carbon atoms which supposes the possible formation of four diastereomers.…”