Journal of Organic Chemistry p. 887 - 891 (1993)
Update date:2022-07-31
Topics:
Vijn, Robert J.
Arts, Henricus J.
Maas, Peter J.
Castelijns, Anna M.
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.Alkaline hydrolysis gave the corresponding 2-aminopyridines in overall yields of 40-65 percent, 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).
View MoreContact:+86-574-87065746
Address:10th Floor, No.787 Baizhang East Road,
Yancheng Creator Chemical Co., Ltd
Contact:0086-515-88710008 88710068 88710858 88710868
Address:No.21 Renming Road, Longgang Town, Yandu County,Yancheng City
Chemsky(shanghai)International Co.,Ltd.
Contact:0
Address:0
Jiangxi Hito Chemical Co., Ltd.
Contact:+86-792-3170318
Address:No. 6, Tianhong Ave., Xinghuo Industry Park, Yongxiu, Jiujiang, Jiangxi, China
Nanjing Vincero International Trading Co.,Ltd
Contact:8618936897229
Address:NO.68, ZhuShan Road, JiangNing WanDa Plaza, Building E Room 1703
Doi:10.1016/j.tetlet.2012.08.025
(2012)Doi:10.1021/jo301693d
(2013)Doi:10.1039/c3dt33039g
(2013)Doi:10.1016/j.tetlet.2014.12.136
(2015)Doi:10.1016/j.dyepig.2012.05.010
(2012)Doi:10.1002/chem.201904220
(2019)