Dicarboxylic acid derivatives

Cyclohexaamylose continued) mono-6-O-tosyl-, preparation of, 23 250 pyridine-2,5-dicarboxylic acid derivative, catalytic action of, 23 251 separation of, by complexing, 23 214 structure, stereochemistry and physical properties of, 23 210-213... 

Pyrroles are obtained by reduction of 1,2-diazines (80JMC481). This reaction has been used in conjunction with inverse electron demand Diels-Alder reactions to prepare 3,4-disubstituted pyrrole-2, 5-dicarboxylic acid derivatives(Scheme 67). Silyl enol ethers or enamines can also serve as the electron-rich dienophiles thus, silyl ethers of ester enolates give 3-methoxypyrroles (84JOC4405). 

Synthesis of Thiophene-2,5-Dicarboxylic Acid Derivatives from Thiodiacetates... 

A conjugated oligomer is synthesized through the palladium-catalyzed decarboxylative coupling of pyrrole-2,5-dicarboxylic acid derivatives with dibromoarenes (Scheme 4.45) [50]. 

In spirooxaziridines like (114), /3-scission proceeds with ring opening. Stoichiometric amounts of iron(II) salt in acidic solution lead to the dicarboxylic acid derivative (115). The radical undergoes some interesting reactions with added unsaturated compounds. For example, pyridine yields a mixture of 2- and 4-alkylation products in 80% yield. Catalytic amounts of iron(II) ion are sufficient here since the adduct of the radical with pyridine is oxidized by iron(III) ion to the final product (116), thus regenerating iron(II) ion (68TL5609). 

Table 2. 1,4-Diazocine Derivatives by the Condensation of 1,2-Dicarboxylic Acid Derivatives with Arene-1.2-diamines...

It was recently found that the free monocarboxylic and dicarboxylic acids derived from pyrethrum hydrolysis will pass through the gas chromatograph and present suitable responses. When this is followed up, it is expected that the method will be simplified and provided better over-all recoveries. 

Di- and mono-esters of phthalic acid, an ortho-dicarboxylic acid derivative of benzene. These compounds are widely used as industrial plasticizers to coat polyvinylchloride surfaces of plastics used in food packaging and medical devices (iv drip bags, blood storage bags, etc.) and are common environmental contaminants. Several phthalate mono-esters are peroxisome proliferator chemicals and can activate the peroxisome proliferator-activated receptor PPAR. 

Bromovinyl)trimethylsilanc, 58, 153, 157 Butadiene-2,3-dicarboxylic acid, derivatives,... 

Polycondensation of dicarboxylic acid derivatives and glycols to polyesters... 

So far, various dicarboxylic acid derivatives, dicarboxylic acids, their activated and non-activated esters, cyclic acid anhydrides, and polyanhydrides have been polymerized with glycols through lipase catalysis to give polyesters. 

Various combinations of dicarboxylic acid derivatives and glycols enzymatically afforded polyesters under mild reaction conditions. Dicarboxylic acids as well as derivatives, activated and non-activated esters, cyclic acid anhydride, and polyanhydrides, were found to be useful as monomer for the enzymatic synthesis of polyesters. 

An analogous result was obtained by the hydrogenation of five-membered cyclic nitronate. The latter reaction afforded a-oximino-Y-hydroxypentane-1,5-dicarboxylic acid derivative (Scheme 3.116, Eq. 2) in high yield (83%) (319). 

A structurally rather dissimilar pTyr mimic was developed by the Boehringer Ingelheim group, namely a triazole-dicarboxylic acid derivative 31 [130], which was shown to yield highly active Lck SH2 domain antagonists. 

Oxidation of benzotriazoles and other fused triazoles by potassium permanganate is a well-established route to lif-triazole 4,5-dicarboxylic acid derivatives. Many of the triazolo[d]pyrimidines, synthesized as purine analogs, can be degraded to monocyclic triazoles by acidic or basic hydrolysis (in other triazolopyriraidines, however, the triazole ring is cleaved preferentially ), e.g. Scheme 24. 

The 7-azabicyclo[2.2.1]heptene derivative (57) decomposes in hot aqueous sodium carbonate solution to give A-benzylpyrrole-3,4-dicarboxylic acid and, presumably, ethylene. Furan-3,4-dicarboxylic acid derivatives are formed analogously on heating the 7-oxabicyclo-[2.2.1]heptene diesters (58). The only thermal decomposition of a... 

The natural extension of this series to the quinoline analog of AC 252,925 was then undertaken. The synthesis route used is based on the work of E. C. Taylor which employed anthranil as a precursor to a quinoline-2,3-dicarboxylic acid derivative (11). The sequence is shown in Scheme V. 

The reaction of 22, with isoprene was also found to proceed smoothly in 1,3,5-TMB to afford the 4-methylcyclohexene-l,2-dicarboxylic acid derivative 21 in 92% ee. 

Finally, the fourth type of replacement in the side acyl region of penicillins is the replacement by dicarboxylic acid derivatives (carbenicillin, ticarcillin). 

Table 2 Monomer stacking parameters for the crystals of topochemically polymerizable 1,3-diene mono- and dicarboxylic acid derivatives [16] ...

Fig. 13 Stereoregular polymer sequences for trans-lA polymers obtained from 1,3-diene dicarboxylic acid derivatives...

Chemical Class Mast cell stabilizer pyranoquinoline dicarboxylic acid derivative Clinical Pharmacology ... 

The dicarboxylic acid derivative 267a is converted directly to the anhydride 268 by treatment with either acetyl chloride or thionyl chloride (Equation 94) <1999SC4141>. 

The condensation of a pyridazine-2,3-dicarboxylic acid derivative with hydrazine remains a favored method for the formation of pyridazino[4,5-f]pyridazines. In the examples generalized in Scheme 5, the presence of an excess of hydrazine hydrate results in formation of the bis(acylhydrazide), which undergoes cyclization in dimethylformamide (DME) to give the 8-hydrazinopyridazino[4,5-f]pyridazine <200181861, 2004JHC647>. 

The reaction of a pyridazine, 5 dicarboxylic acid derivative with hydrazine remains a favored approach for the preparation of pyridazino[4,5-4 pyridazines <2000TL2863, 2002JCCS217>, and di- /t-butyl hydrazodicarboxylate has been used as a hydrazine substitute in the presence of perhydro derivatives, as illustrated in Equation (6) <1993JPC13408>. 

Fronchimont Reaction. By the action of f CN on a-bromo acids or esters, a-cyano-a,j8-dicarboxylic acid derivatives are formed which on hydrolysis and decarboxylation yield a,/8 dicarboxylic acids ... 

The selective carbonylation of 4,7-dichloroquinoline proceeds readily and the chlorine in the more active 4-position reacts preferentially to give quinolinecarboxylic acid derivatives in excellent yield (7.65.), The carbon-chlorine bond in the 7-position is so unreactive that attempts at the preparation of dicarboxylic acid derivatives were only moderately successful.86... 

Other 2,3-Diphosphoglycerate Pocket Cross-Linkers, The reactivity of the valine NAl(l)a and lysine EF6(82)p residues in the 2,3-DPG pocket shown by NFPLP and (bis-PL)P4 has stimulated the search for other reagents that react similarly but have potential for greater efficiency and ease of scaleup. The systematic study of four different dicarboxylic acid derivatives, cross-linked in both oxygenated and deoxygenated conditions, has been reported (92). Each of these derivatives presents problems in purification, and proof of the sites of reaction is tedious. 

Hi) Carboxylic acids and derivatives. The haloform reaction on thienyl methyl ketones leads to thiophenecarboxylic acids, which can be treated with Raney nickel to produce the open-chain acids. This method has been used for the five-carbon homologation of carboxylic acids and to produce dicarboxylic acids (Scheme 51). Long-chain carboxylic acids may also be prepared by using dicarboxylic acid derivatives for the acylation of thiophenes (Scheme 52). In the synthesis of Queen substance, the precursor (213) has been generated by Raney nickel desulfurization of the appropriate thiophene-2-acetic acid derivative (79T329). 

Some novel bicyclic pyrylium salts arise when a dicarboxylic acid derivative is used. For example, although decanedioyl chloride did not diacylate isobutene, possibly because of strain inherent in the expected product, 1,12-dodecanedioyl chloride gave a very low yield of the pyrylium salt (658) (62T1079). A dilute solution of the reactants in nitromethane was used in order to favour the intramolecular reaction. In a similar vein, a macrocyclic alkene, such as cyclododecene, undergoes diacylation to the bicyclic salt (659) (68TL4643), whilst... 

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