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Name Reactions
Published in Benny K.G. Theng, Clay Mineral Catalysis of Organic Reactions, 2018
The Biginelli reaction or Biginelli pyrimidone synthesis, is an acid-catalyzed multicomponent condensation reaction involving an aromatic aldehyde, such as benzaldehyde (1), ethyl acetoacetate (2), and urea (3) to yield 3,4-dihydropyrimidin-2(1H)-one (4) as shown in Scheme 5.6. The homogeneous reaction is commonly carried out by refluxing the components in ethanol with HCl as catalyst. The mechanism, pharmacological applications, and scope of the Biginelli reaction have been reviewed by Suresh and Sandhu (2012).
Organic Synthesis
Published in Suresh C. Ameta, Rakshit Ameta, Garima Ameta, Sonochemistry, 2018
Chetna Ameta, Arpit Kumar Pathak, P. B. Punjabi
The Biginelli reaction is a multicomponent reaction that gives 3,4-dihydropyrimidin-2(1H)-ones from ethyl acetoacetate, an aryl aldehyde (such as benzaldehyde) and urea. This reaction was developed by Biginelli (1893). The reaction can be catalysed by Bronsted acids and/ or by Lewis acids such as copper(II) trifluoroacetate hydrate and boron trifluoride (Kappe, 1993).
Highly regioselective, base-catalyzed, biginelli-type reaction of aldehyde, phenylacetone and urea/thiourea kinetic vs. thermodynamic control
Published in Journal of Sulfur Chemistry, 2018
Manijeh Nematpour, Elham Rezaee, Mehdi Jahani, Sayyed Abbas Tabatabai
Biginelli reaction is an acid(base)-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) using multicomponent condensation of easily-accessible starting materials, including (thio)urea, active methylene compound and aldehyde [1–5]. DHPMs are an interesting pharmacophore in the medicinal chemistry and fascinating target for combinatorial chemistry of biologically active heterocycles with novel properties in the past two decades [6–8]. Also, DHPM was applied as a key core in the synthesis of wide variety pharmaceutical compounds, significant biomolecules, diverse natural products and interesting alkaloids with special properties [9] and functional materials such as adhesive [10], polymers and fabric dyes [11]. Furthermore, some of the DHPMs show many attractive properties such as antiviral, antibacterial, antitumour, antimalarial, anti-inflammatory, antidiabetic, antitubercular, antileishmanial, anti-epileptic, antiproliferative activities, etc. [12–16]. A number of polysubstituted DHPMs have been found to be antihypertensive agents, potent calcium channel blockers [17], A2B receptor antagonists [18] and mPGES-1 inhibitors [19]. Presently, the Biginelli reaction is exploited in solid-phase synthesis for heterocyclic compound [20] and asymmetric synthesis for bioactive chiral DHPMs [21]. Despite extensive studies on the Biginelli-type reactions, achieving to new approaches in synthesis of DHPMs with various substitutions in mild reaction conditions is a great deal of attention. The standard protocol for the Biginelli reaction generally involves the use of a Lewis or protic acid [22–25] and few methods are available under basic conditions. In addition, most reported Biginelli-type protocl led to formation of thermodynamic compunds.
One pot synthesis of bis (dihydropyrimidinone) and tetrahydro-4H-chromenes derivatives using Ag2O/GO/TiO2 composite nanostructure
Published in Inorganic and Nano-Metal Chemistry, 2023
Fatemeh Samandi Zadeh, Mohammad Kazem Mohammadi, Ayeh Rayatzadeh, Neda Hasanzadeh
The Biginelli reaction is one of the well-designed methodologies used for the synthesis of DHPM or thione derivatives, an important family of compounds known for their diverse pharmacological properties which can act as antibacterial, antiviral, and calcium channel modulators as well as anticancer and antihypertensive agents. The reported biological activities of DHPMs encourage research groups to produce structurally diverse libraries of bioactive heterocycles.[18–21]