Glutaconate

Condensation of the fragment A with dimethyl /J-methyl glutaconate, funher condensation with the fragment B, and the completion of the synthesis ... 

Maleic, fumaric, glutaconic, citraconic, mesaconic and itaconic acid... 

Little is known concerning the tautomerism of glutaric anhydrides and related compounds, although a recent report claims the isolation of the two tautomeric forms (18 and 19) of a glutaconic anhydride derivative, which appears improbable. 

Reactions of glutaconic acid derivatives with heterocycles 980PP657. 

Synthesis of heterocycles from glutaconic acid derivatives 980PP657. 

Glutaconic aldehyde dianiiide, m synthesis of heptamethine thiazolocyanines, 57... 

Reaction between Deuterium Oxide and cis- and trans-Glutaconic Acids. J. chem. Soc. [London] 1939, 1673. 

However in certain cases no reagent is used shows that the mechanism is not so simple. Further in the conversion of cis glutaconic acid into the trans form has thrown light that unexpected phenomena may occur in what seem to be very simple reactions and may sometimes lead to erroneous conclusions. 

Quoted in Seddon, (1972 41), from C. K. Ingold, E. A. Perren, and J. F. Thorpe, "Ring-Chain Tautomerism. Pt. III. The Occurrence of Tautomerism of the Three-Carbon (Glutaconic) Type between a Homocyclic Compound and Its Unsaturated Open-Chain Isomeride," JCS 121 (1922) 17651789. 

The epoxidation of alkenes is one of the most impoi4ant oxidation methods. Electrochemical epoxidation of electron-poor olefins such as enoates (154 155) and enones has been accomplished by using silver(III)oxo bis(2,2 -bipyridine) and similar complexes (Scheme 61) [241], )-Dimethyl glutaconate is electrolyzed in an MeCN-LiCl04/Ag0Ac)(bpy)-(Pt) system to give the trans-epoxide in 90% yield. 

Scheme 1. Principle of cyanine dye synthesis leading to trimethine (n = l), pentamethine (n = 2) and heptamethine (n = 3) chromophores. Structures comprising indolic subunits are usually named indocarbocyanine, indodicarbocyanine and indotricarbocyanine, respectively. Formic acid, malonic aldehyde, glutaconic aldehyde are used in their protected dianUide or orthoester form. They can be applied as substituted derivatives to introduce residues into the polymethine unit. The indolic substructure might bear further residues or annelated aromatic rings...

The Pechmann and Knoevenagel reactions have been widely used to synthesise coumarins and developments in both have been reported. Activated phenols react rapidly with ethyl acetoacetate, propenoic acid and propynoic acid under microwave irradiation using cation-exchange resins as catalyst <99SL608>. Similarly, salicylaldehydes are converted into coumarin-3-carboxylic acids when the reaction with malonic acid is catalysed by the montmorillonite KSF <99JOC1033>. In both cases the use of a solid catalyst has environmentally friendly benefits. Methyl 3-(3-coumarinyl)propenoate 44, prepared from dimethyl glutaconate and salicylaldehyde, is a stable electron deficient diene which reacts with enamines to form benzo[c]coumarins. An inverse electron demand Diels-Alder reaction is followed by elimination of a secondary amine and aromatisation (Scheme 26) <99SL477>. 

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