Tetrahedron p. 13097 - 13110 (1996)
Update date:2022-08-02
Topics:
Noguchi, Michihiko
Mizukoshi, Takashi
Uchida, Takehiko
Kuroki, Yoshiaki
A mechanistic proposal for the azepine-ring formation at the periphery of heterocyclic systems is described. Intramolecular thermal ene reactions of O-alkyl oximes 5 and 6, N',N'-disubstituted hydrazone 11, and N-tosyl imines, obtained from aldehydes of pyrido[1,2-a]-pyrimidine 1, pyridine 2, and pyrimidine system 3, have been developed. These reactions reveal to be a fruitful and stereoselective approach to the azepine derivatives fused by heterocycles. The mechanistic discussions on the azepine-ring formation through the imine and carbonyl ene reactions have been accomplished by the kinetic studies as well as the molecular orbital calculations (PM3 method) of the model reactions. These results demonstrate that both ene reactions proceed in a concerted manner.
View MoreTianjin Dongchang Fine Chemical Industry Co., Ltd.
Contact:+86-22-29894595
Address:Economic Developing Zone, Ji County, Tianjin, China
Contact:+86-10-83993285
Address:Rm.1708, Haobai Tower, Building 6, No.50, North Road, West Third Ring, Haidian District, Beijing, China
Nanjing Qirui Material Co., Ltd.
Contact:+86-25-52320053
Address:F4-5, #17 Building, Chuang Yi Yuan, No.6 Guanghua East Street, Nanjing, 210007 P.R.China
Beijing Stable Chemcial Co.ltd
Contact:86-10-63785052
Address:A1301 Technological Edifice. No.4 FuFeng Road,FengTai District, Beijing. China
website:http://www.oceanchem-group.com
Contact:86-536-8596048
Address:9th floor,Building B future Plaza, No.88.Fenghuang Street,Weifang,Shandong,China
Doi:10.1016/0040-4039(96)01703-0
(1996)Doi:10.1007/s00706-007-0656-8
(2007)Doi:10.1002/jhet.5570240331
(1987)Doi:10.1002/hlca.19570400233
(1957)Doi:10.1021/om8000394
(2008)Doi:10.1002/anie.200704609
(2008)