293306-35-1Relevant academic research and scientific papers
Isothiazoles. Part 11: 3-Azahexatrienes from 2-arylpropenamidines: Electrocyclization to 6-aminonicotinic acid derivatives
Beccalli, Egle M.,Clerici, Francesca,Gelmi, Maria Luisa
, p. 4817 - 4821 (2000)
A new synthesis of 6-aminonicotinic acid derivatives was developed starting from the readily available 3-substituted acrylamidines 1 and electron-poor alkynes 2. By nucleophilic addition of the basic amidinic NH to the electron-poor triple bond, the intermediate azatrienes 4 were obtained. Through thermally induced electrocyclization compounds 4 afforded the pyridines 3 by alcohol elimination or oxidation. Another approach was the direct cyclization of acrylamidines with the dienyne system as a backbone. (C) 2000 Elsevier Science Ltd.
