Journal of Organic Chemistry p. 11114 - 11124 (2019)
Update date:2022-08-05
Topics:
Zhao, Yun-Long
Cheng, Ying
We report herein our serendipitous discovery of the rapid and straightforward accesses to unprecedented diverse complex molecular structures from readily available starting materials. Catalyzed by 1,8-diazabicyclo[5.4.0]undec-7-ene under mild conditions, o-(1-(acyloxy)propargyl)benzaldehydes 1 underwent efficient and selective dimerization reactions to produce novel complex bisether-bridged tricyclic products 3 and 4. The reactions proceeded most probably through dimerizations between 3-methylene-3H-isochromene intermediate and its zwitterionic resonance structures which were generated from a concerted 6-πelectrocyclic ring closure reaction from the initially formed (2-formylphenyl)allene intermediates derived directly from o-(1-(acyloxy)propargyl)benzaldehydes. Treatment of the resulting product simply with NaOEt in ethanol and aqueous HCl, respectively, enabled further development of complex molecular diversities.
View MoreZibo Jujin Chemical Industry Co., Ltd.(Dongming Jujin Chemical Industry Co., Ltd. )
Contact:+86-533-2975022
Address:No.99 Shanquan Road, Zhangdian District
website:http://www.guarson.com
Contact:+86-523-88059600,+86-13805268803
Address:Room B1006,Yafang Building,Jiangyan Avenue,Jiangyan District, Taizhou City,Jiangsu,China
Shangdong Shinning Pharm co.ltd
Contact:18866891188
Address:Taishan Road, Ningyang Economic Development Zone, Tai'an, Shandong
Tianjin Anda North Industrial & Business Co.Ltd.
Contact:86-22-24999306
Address:No.11 Erwei Road,Dongli Development Area,Tianjin,China
HAINAN JINYING IMPORT AND EXPORT CO. LTD
Contact:+86-898-32875423
Address:A SECTION 19TH FL, TIMES SQUARE, NO.2 GUO MAO AVENUE HAIKOU, HAINAN, P. R. OF CHINA
Doi:10.3184/030823407X200047
(2007)Doi:10.1021/jo01029a036
(1964)Doi:10.1021/jo01260a031
(1969)Doi:10.1080/00397919708005450
(1997)Doi:10.1002/cber.19971301116
(1997)Doi:10.1039/a706586h
(1997)