Journal of the American Chemical Society p. 7743 - 7752 (1981)
Update date:2022-09-26
Topics:
Taylor, Edward C.
Haley, Neil F.
Clemens, Robert J.
Treatment of α-chloroacylhydrazones of diaryl and certain aralkyl and dialkyl ketones with sodium hydride in anhydrous tetrahydrofuran gives 1-(disubstituted methylene)-3-oxo-1,2-diazetidinium inner salts (ylides). The reaction pathway involves formation of the hydrazone anion followed by intramolecular SN2 halide displacement (with complete inversion at the α carbon) by the sp2 imine nitrogen. These 1-(disubstituted methylene)-3-oxo-1,2-diazetidinium ylides are reduced by sodium borohydride to give 1-substituted 1,2-diazetidin-3-ones, undergo dipolar cycloaddition reactions to give fused aza-β-lactams, and can be hydrolyzed with p-toluenesulfonic acid monohydrate to the p-toluenesulfonic acid salt of 1,2-diazetidinone.
View MoreContact:+86-512-56795332
Address:No227 Shuanglong Rd, Fenghuang, Zhangjiagang
Suzhou Chiral Pharmaceuticals Co., Ltd.
Contact:86-0512-63197058
Address:Building A, No. 2358, Chang'an Road, Wujiang Science Park
Shangyu Sanhechemicals Co.,LTD.
Contact:86-0571-56696839
Address:Num.2952,Nanhuan Road,Binjiang District,Hangzhou,China
Dalian Join King Biochemical Tech. Co., Ltd.
Contact:0411 39216206
Address:814 First State Blvd
Shanghai Rainbow Chemistry Co., Ltd.
Contact:+86-21-64968086-5815/5812
Address:3rd floor, Building 7, 251 Faladi Road, Zhangjiang Hi-Tech Park, Pudong District, Shanghai, P.R. China
Doi:10.1016/S0957-4166(01)00010-6
(2001)Doi:10.1007/BF00506034
(1981)Doi:10.1016/0022-1139(95)03290-T
(1995)Doi:10.1007/BF00899780
(1981)Doi:10.1021/jo00340a021
(1982)Doi:10.1016/S0040-4039(00)99931-3
(1984)