Cyanocarboxylic acids

The a-bromo or a-chloro carboxylic acids 2 are versatile intermediates for further synthetic transformations. For example they can be converted into a-hydroxy carboxylic acids by reaction with water by reaction with cyanide a-cyanocarboxylic acids 7 are obtained, which can be further converted to... 

Zhu, D., Mukherjee, C., Biehl, E.R. and Hua, L. (2007) Nitrilase-catalyzed selective hydrolysis of dinitriles and green access to the cyanocarboxylic acids of pharmaceutical importance. AdviOU cd Synthesis and Catalysis, 349, 1667-1670. 

The a-amino acid alanine is cleaved to acetonitrile whilst the s-amino acid 6-aminohexanoic acid is dehydrogenated in excellent yield to the cyanocarboxylic acid. 

Eisele, Grob, Renk and Tschammer (122) have reported the quantitative transformation of the bicyclic ketone oximetosyiate 435 into the cyanocarboxylic acid 437. This reaction occurs through the intermediate 436 and it is interesting to note that the formation of the nitrile function occurs through an anti elimination process. 

Most dicarboxylic acids are prepared by adaptation of methods used to prepare monocarboxylic acids. Where hydrolysis of a nitrile yields a monocarboxylic acid, hydrolysis of a dinitrile or a cyanocarboxylic acid yields a dicarboxylic acid where oxidation of a methylbenzene yields a benzoic acid, oxidation of a di-methylbenzene yields a phthalic acid. For example ... 

Short pulses of laser radiation are used, typically at 337 nm, (nitrogen laser) but UV or infrared (IR) lasers can also be employed, depending on the matrix compound selected. Common matrix compounds are 2,5-dihydroxybenzoic acid, nicotinic acid, sinapinic acid, and a-cyanocarboxylic acid.6... 

As shown in Eq. 63, the bicyclic species 216 is quantitatively transformed into the ra-cyanocarboxylic acid 218 [32]. The intermediate species 217 formed from the reaction with hydroxide ion has two electron pairs, one on each of the two oxygen atoms located on Cl, antiperiplanar to the CTci-c2 bond. The antiperiplanar relationship between other requirements for the overall fragmentation to be successful. Note that the nitrile function emerges from a process of anti-elimination. 

Potqssiam hydroxide/alcohol Nitriles from a-cyanocarboxylic acid esters... 

Carboxylic acids from a-cyanocarboxylic acid amides... 

Hydrochloric acid Carboxylic acid imides from cyanocarboxylic acids... 

Poly(l,2,4-triazole)s can be obtained by the reaction of dinitriles with dihydrazides or by heating cyanocarboxylic acids. They are found to be resistant to high temperatures, especially when they contain aromatic compounds in the polymer chain. 

Without additional reagents a-Cyanocarboxylic acids from 5-isoxazolones... 

The catalytic, asymmetric and decarboxylative Mannich-type reaction involving a nucleophile generation from cyanocarboxylic acids (617) via... 

Chloroformic acid esters triethylamine Cyanocarboxylic acid esters from dicarboxylic acid monoamides... 

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