Quinoline-2,3-dicarboxylates, 4-hydroxy

Fischer indole cyclization and transformation of a nitrile to an ester (Pinner synthesis) to yield diethyl 5-hydroxy-1 T/-pyrrolo[2,3-/]quinoline-2,7-dicarboxylate (183) was performed in one step by... 

Complexation also offers attractive possibilities for selective recovery of dicarboxylic acids, hydroxy-carboxylic acids (luetic, citric, etc.), phenolic carboxylic acids (gallic, vanillic, caffeic. etc.), amino acids, quinolines, and alkaloids from aqueons solution. 

This reaction was initially reported by Diels and Reese in 1934. It is the conjugate addition between hydroazobenzene and dimethyl acetylene-dicarboxylate. The resulting adduct can be transformed into three different heterocyclic compounds under various experimental conditions (i.e pyrazolones with acid, indoles upon heating in xylene, and quinolones with base ). For example, l,2-diphenyl-3-carbomethoxy-5-pyrazolone will be generated from the adduct in acetic acid (acidic condition), whereas dimethyl indole-2,3-dicarboxylate is produced in xylene (neutral condition) and 2-hydroxy-3-anilino-4-carbomethoxy-quinoline is yielded in pyridine (basic condition). The latter can be further converted into 2,3-dihydroquinoline upon decarboxylation and hydrolysis." This reaction has been extended to heat the 1 1 adduct in picoline. ... 

Diethylenetriaminepentaacetic acid Glycoletherdiaminetetraacetic acid Trimethylenetetraaminehexaacetic acid QuinoIine-2-carboxylic acid QuinoIine-8-carboxylic acid 8-Hydroxy quinoline 1,10-PhenanthroIine 2-Methyl-l,10-phenanthroIine 5-Methyl-l,10-phenanthroIine 2,9-Dimethyl-l,10-phenanthroIine 4,7-Dimethyl-l,10-phenanthroIine Pyridine-2-carboxylic acid Pyridine-2,3-dicarboxylic acid Pyridine-2,4-dicarboxylic acid Pyridine-2,6-dicarboxylic acid. 

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