Journal of Organic Chemistry p. 4006 - 4014 (1988)
Update date:2022-08-05
Topics:
Knapp, Spencer
Levorse, Anthony T.
The synthesis of a series of iodo lactams has been achieved by a new cyclization method that depends on generating N,O-bis(trimethylsilyl)imidate derivatives as intermediates.Treatment of an unsaturated amide with trimethylsilyl triflate in pentane and then iodine in tetrahydrofuran gives the iodo lactam.Some reactions of this new difunctional group with bases, nucleophiles, and Michael acceptors leading to functionalized or elaborated lactams are presented.In general, iodo lactams undergo direct SN2 reactions with reactive (but weakly basic) nucleophiles like azide and triphenylphosphine and elimination or decomposition in the presence of bases or basic nucleophiles.Sodium hydride may be used to generate an N-acylaziridine intermediate, which can be opened with azide to deliver an azido lactam with overall retention of stereochemistry.Silver-assisted solvolysis of iodo lactams gives the hydroxy lactams with retention of configuration, probably also because of participation by the lactam nitrogen.The sodium salt of 5-(iodomethyl)-2-pyrrolidinone (3), generated at -20 deg C, undergoes an annulation reaction with unsaturated esters (but not sulfones), leading to pyrrolizidine derivatives.
View MoreNanjing HuiBaiShi Biotechnology Co.,Ltd.
Contact:+86 (25)58745219
Address:No.606 Ningliu Road,LiuHe District.
Tianjin Tensing Fine Chemical Research Develop Centre
Contact:86-022-23718576,13032267585
Address:2-2-201,13 Guiyuan road,Huayuan Industry district,Tianjin,china
Contact:86-25-58619180
Address:Nanjing High-Tech Zone 10 Xinghuo Road Pukou District Nanjing, Jiangsu 210061 The People's Republic of China
Contact:+86-519-86623222
Address:29F/D, 99 Yanling West Road, Changzhou, Jiangsu, China
Beijing Greenchem Technology Co.,Ltd. ( Panjin Greenchem Technology Co.Ltd .)
website:http://www.bjgreenchem.com/
Contact:+86-427-6515887
Address:301,302, 3rd Floor, Building C-7, Dongsheng Science Park, Northern Territory, Zhongguancun, No. 66, Xixiaokou Road, Haidian District, Beijing
Doi:10.1246/bcsj.62.3598
(1989)Doi:10.1021/om00099a013
(1988)Doi:10.1039/c39870001718
(1987)Doi:10.1016/j.bmcl.2011.07.021
(2011)Doi:10.1016/j.ejmech.2008.09.047
(2009)Doi:10.1016/0022-328X(87)85133-1
(1987)