Journal of Organic Chemistry p. 79 - 83 (1987)
Update date:2022-07-30
Topics:
Confalone, Pat N.
Huie, Edward M.
A synthetic route for the conversion of carbon-bridged dibenzocycloheptanes and dibenzazepines, readily available by intramolecular <3 + 2> cycloaddition methodology, to carbon-bridged dibenzazocines and dibenzodiazocines is presented.The key transformations invovle the Beckmann rearrangement of intermediates 5, 12, 14, and 15 to the various possible lactam products.Factors controlling the observed regiochemistry of the rearrangement process, leading to regiochemical control of the Beckmann products, are discussed from a mechanistic viewpoint.A rationale for the observed selectivity in the hydride reduction of the urethane lactams 16, 21, 22, and 24 is also presented.The overall approach affords a facile and generally useful transformation of olefin aldehydes of general structure D to the bicyclics F and/or G via the cycloadducts E.
View MoreZhushan County Tianxin Pharmaceutical & Chemical Co., Ltd.
Contact:0086-719-4224892
Address:Tutang Road, Chengguan Town, Zhushan County, Hubei Province
Suzhou SuKaiLu Chemical Technology Co., Ltd.
Contact:+86-512-62766020
Address:Floor 4, Building 1, Xinyi Pharmaceutical Valley Wisdom Industrial Park, 415 Changyang Street, Suzhou Industrial Park, Jiangsu Province
Daicel Chiral Technologies (China)CO.,LTD
Contact:021-5046-0086*8
Address:Part C, FL 5, the 16th Building, No. 69, XiYa Road, WaiGaoQiao Free Trade Zone, Shanghai, 200131, P.R.China
Tianjin Pharmacn Medical Technology Co.,Ltd.
Contact:86-22-60122566ext.866(English),23359620
Address:Green Industrial Base, 6 Haitaifazhan Sixth Rd., Huayuan Industrial Area, Tianjin, 300384, China
Beijing Stable Chemcial Co.ltd
Contact:86-10-63785052
Address:A1301 Technological Edifice. No.4 FuFeng Road,FengTai District, Beijing. China
Doi:10.1021/jo005540t
(2001)Doi:10.1002/cbic.201300325
(2013)Doi:10.1016/0022-328X(86)82032-0
(1986)Doi:10.1016/j.tet.2008.06.044
(2008)Doi:10.1021/om800464y
(2008)Doi:10.14233/ajchem.2013.13649
(2013)