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The reaction mechanism of the Biginelli reaction is a series of bimolecular reactions leading to the desired dihydropyrimidinone. [14]According to a mechanism proposed by Sweet in 1973 the aldol condensation of ethylacetoacetate 1 and the aryl aldehyde is the rate-limiting step leading to the carbenium ion 2.
Biginelli's first known scientific work, in which he was a co-author of his mentor Icilio Guareschi, was focused on synthesis and reactivity of chlorobromonaphthalene. [10] [11] Already in the University of Florence, Biginelli described a three-component reaction between urea, aldehyde, and ethyl acetoacetate, which was at first incorrectly interpreted as one leading to the formation of alpha ...
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In organic chemistry, a rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule. [1] Often a substituent moves from one atom to another atom in the same molecule, hence these reactions are usually intramolecular.
Different aromatic nitrogen heterocyclic compounds proceed through the Chichibabin reaction in a matter of minutes and others can take hours. Factors that influence the reaction rate include: Basicity - The ideal pKa range is 5-8 and the reaction either does not proceed, or proceeds poorly outside of this range. The reaction occurs faster under ...
C.Oliver Kappe is the leader in Biginelli reactions in the chemistry world. He mentions in the paper Recent Advances in the Biginelli Dihydropyrimidine Synthesis. New Tricks from an Old Dog (Kappe, C.O.; Acc. Chem. Res., 2000, 33, 879-888) that the mechanism has been determined as first a condensation between the benzaldehyde and urea, not the ...
A multi-component reaction (or MCR), sometimes referred to as a "Multi-component Assembly Process" (or MCAP), is a chemical reaction where three or more compounds react to form a single product. [1] By definition, multicomponent reactions are those reactions whereby more than two reactants combine in a sequential manner to give highly selective ...
The reaction is acid catalyzed and the reaction type is nucleophilic addition of the amine to the carbonyl compound followed by transfer of a proton from nitrogen to oxygen to a stable hemiaminal or carbinolamine. With primary amines, water is lost in an elimination reaction to an imine. With aryl amines, especially stable Schiff bases are formed.