1172626-91-3Relevant academic research and scientific papers
0-amine-assisted cannizzaro reaction of glyoxal with new 2,6-diaminoanilines
Irie, Yuhki,Koga, Yuji,Matsumoto, Taisuke,Matsubara, Kouki
experimental part, p. 2243 - 2250 (2009/08/09)
The preparation of several new o-amine-substituted anilines was achieved according to a new bifunctional molecular design, and their reactions with glyoxal were conducted. Can- nizzaro reactions of glyoxal proceeded using specifically designed anilines, such as 2,6-dipyrrolidinyl-, 2,6-dipiperidinyl-, 2,6-dimorpholinyl-, and 2-pyrrolidinyl-aniline, which are new and can easily be synthesized by substitution of halogen-substituted nitrobenzene with amines and subsequent reduction with hydrogen, to form a-hydroxy acetamide and a-amino acetamide derivatives, as a result of the Cannizzaro reaction. In comparison with the reaction of glyoxal with p- pyrrolidinylaniline to form a common diimine product, the reaction with o-pyrrolidinylaniline leads only to a-hydroxy amides, strongly suggesting that the abnormal Cannizzaro reactions are attributed to the existence of basic nitrogen atoms at the o-positions, which suppress diimine formation and assist the generation of acetamides.
