Interaction of ethyl 2-cyano-3-oxobutyrate and an arylamine salt yields a 1-aryl-5-cyano-1,2-dihydro-2-imino-pyridine and an ethyl 3-arylamino-2-cyanocrotonate. The 1-aryl-2-iminopyridines are hydrolysed by water to 1-aryl-2-pyridones and with alkali undergo the Dimroth rearrangement to 2-arylaminopyridines. Ethyl 3-arylamino-2-cyanocrotonates are readily cyclised to 3-cyanoquinolines.
R. J. Grout, B. M. Hynam and M. W. Partridge, J. Chem. Soc. C, 1969, 1590 DOI: 10.1039/J39690001590
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