Efficient Synthesis of 4-oxo-4,5-dihydrothieno[3,2-cc]quinoline-2-carboxylic Acid Derivatives from Aniline
The first reported synthesis of potential kinase inhibitors, 4-oxo-4,5-dihydrothieno[3,2-c]quinoline-2-carboxylic acid derivatives starting from aniline is described. This efficient high yielding sequence was carried out in six steps without any chromatographic purification. A tandem nucleophilic aromatic substitution/cyclization reaction was used as a key step in the sequence. The versatile intermediate 2-carboxylic acid was used as a suitable precursor to access the functionalization of the C-ring, by convergent analog synthesis of several novel derivatives.
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Chatterjee, Arindam; Cutler, Stephen J.; Khan, Ikhlas A.; and Williamson, John S., "Efficient Synthesis of 4-oxo-4,5-dihydrothieno[3,2-cc]quinoline-2-carboxylic Acid Derivatives from Aniline" (2014). Office for Research Publications and Presentations. 33.