Search results
Results from the WOW.Com Content Network
Maleic anhydride is a classic substrate for Diels-Alder reactions. [9] It was used for work in 1928, on the reaction between maleic anhydride and 1,3-butadiene, for which Otto Paul Hermann Diels and Kurt Alder were awarded the Nobel Prize in 1950. It is through this reaction that maleic anhydride is converted to many pesticides and pharmaceuticals.
Maleimide-mediated methodologies are among the most used in bioconjugation. [5] [6] Due to fast reactions and high selectivity towards cysteine residues in proteins, a large variety of maleimide heterobifunctional reagents are used for the preparation of targeted therapeutics, assemblies for studying proteins in their biological context, protein-based microarrays, or proteins immobilisation. [7]
In industry, maleic acid is derived by hydrolysis of maleic anhydride, the latter being produced by oxidation of benzene or butane. [4] Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis. [8] Maleic acid may be used to form acid addition salts with drugs to make them more stable, such as indacaterol ...
The Wagner-Jauregg reaction is a classic organic reaction in organic chemistry, named after Theodor Wagner-Jauregg [] (son of Julius Wagner-Jauregg), describing the double Diels–Alder reaction of 2 equivalents of maleic anhydride with a 1,1-diarylethylene.
3-Sulfolene reacts with maleic anhydride in boiling xylene to cis-4-cyclohexene-1,2-dicarboxylic anhydride, obtaining yields of up to 90%. [4] 3-Sulfolene reacts also with dienophiles in trans configuration (such as diethyl fumarate) at 110 °C with SO 2 elimination in 66–73% yield to the trans-4-cyclohexene-1,2-dicarboxylic diethyl ester. [17]
In organic chemistry, the ene reaction (also known as the Alder-ene reaction by its discoverer Kurt Alder in 1943) is a chemical reaction between an alkene with an allylic hydrogen (the ene) and a compound containing a multiple bond (the enophile), in order to form a new σ-bond with migration of the ene double bond and 1,5 hydrogen shift.
[3] [4] Because the diene is very electron-rich it is a very reactive reagent in Diels-Alder reactions. This diene reacts rapidly with electrophilic alkenes, such as maleic anhydride. The methoxy group promotes highly regioselective additions. The diene is known to react with amines, [5] aldehydes, alkenes and alkynes. [4]
The parent compounds are maleic acid and the isomeric fumaric acid. Maleic acid forms esters, an imide, and an anhydride, i.e. diethyl maleate, maleimide, and maleic anhydride. Fumaric acid, as fumarate, is an intermediate in the Krebs citric acid cycle, which is of great importance in bioenergy.