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 MoreLuojiang Chenming Biological Products Co
Contact:+86 15000297032
Address:GROUP NO.4, HE SHENG VILLAGE, PANLONG TOWN,
ABA Chemicals (Shanghai) Limited
Contact:021- 5115 9199-232
Address:Suite 18D, #201 Ningxia Road,
website:http://www.sigmaaldrich.com
Contact:800 558-9160
Address:Industriestrasse 25CH-9471 Buchs SGSwitzerland
website:http://www.simagchem.com
Contact:+86-592-2680277
Address:21/F Hualong Office Building,No.6 Hubin East Road, Xiamen,China
Hangzhou Gangjin Chemical Co.,Ltd.(expird)
Contact:+86-571-85109780
Address:707 Zhejiang Minhang Bldg., No.290 Zhongshan North Road, Hangzhou 310003, 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)