📜5-酮基已腈置于sodium Hydroxide,硫酸羟胺,乙酰氯体系中,化学反应 6.0H,反应生成 2-乙酰氨基-6-甲基嘧啶
参考文献:Synthesis Of 6-Substituted 2-(N-Acetylamino)Pyridines And 2-Aminopyridines By Cyclization Of 5-Oximinoalkanenitriles
标题:Synthesis Of 6-Substituted 2-(N-Acetylamino)Pyridines And 2-Aminopyridines By Cyclization Of 5-Oximinoalkanenitriles
摘要:Oxime Derivatives Of 5-Oxoalkanenitriles (C6 Chain Or Longer) Were Cyclized In Most Cases With A Combination Of Accl And Ac2O,Or Ac2O And Hcl To 6-Substituted 2-(N-Acetylamino)Pyridines. Hydrolysis Gave The Corresponding 2-Aminopyridines In Overall Yields Of 40-65 %,With The Exception Of Pyridine 3E. Oxime Derivatives Of 5-Oxopentanenitriles Did Not Cyclize But Gave Glutaronitriles Instead. In Some Experiments With 5-Oximinohexanenitrile(1A),2,4-Dimethyl-5-(2-Cyanoethyl)Oxazole (9)Was Detected In Addition To The Main Product,2-(N-Acetylamino)-6-Methylpyridine(2A). Formation Of These Compounds Can Be Explained On The Basis Of A Common Intermediate 7 Formed Through Rearrangement Of The O-Acetylated 5-Oximinohexanenitrile (4).
DOI:10.1021/jo00056A021