106237-22-3Relevant academic research and scientific papers
Preparation and Cyclodehydration of β-Arylaminocrotonaldehyde
Ono, Machiko,Todoriki, Reiko,Tamura, Shinzo
, p. 463 - 470 (2007/10/02)
β-Arylaminocrotonaldehydes (3) were prepared by alkaline hydrolysis of 1-arylamino-3-arylimino-1-butenes (2).On treatment with sulfuric acid, β-anilinocrotonaldehyde (3b) and p-methyl- (3a), m-chloro- (3c), and p-chloro- (3d) derivatives were cyclodehydrated to give the corresponding quinaldines in quantitative yields.The protonation of 3 was proved to take place at the oxygen atom on the basis of spectral evidence.The mechanism of the cyclodehydration is discussed.Keywords-Combes reaction; cyclodehydration; hydrolysis; β-arylaminocrotonaldehyde; 1-arylamino-3-arylimino-1-butene; quinaldine derivative; protonation
