187142-00-3Relevant academic research and scientific papers
Pyridines and pyrimidines from etacrynic acid
Goerlitzer,Diers
, p. 97 - 100 (2007/10/03)
The alkoxy-3-cyano-pyridines 2 are obtained from the alcoholate catalyzed reaction of etacrynic acid (1) with malononitrile. Variation of the acidic hydrolysis of 2 yields the acid derivatives 3-5. Ethyl benzoylacetate reacts with 1 and sodium hydroxide to give the 1,5-diketone 6, which cyclizes with ammonium acetate to form the pyridine 7. The ethyl pyridine-3-carboxylate 8 is received from a one pot reaction. The compounds 9 are formed by Michael addition of the barbituric acids to 1. Melting of 9b with ammonium acetate yields the annulated pyridopyrimidine 10. The pyrimidinethione 11 results from the reaction of 1 with thiourea.
