Journal of Molecular Structure p. 44 - 52 (2018)
Update date:2022-07-29
Topics:
Amirani Poor, Mahboobe
Darehkordi, Ali
Anary-Abbasinejad, Mohammad
Mohammadi, Marziyeh
An intermolecular Ugi reaction of 2-(1-(aminomethyl)cyclohexyl)acetic acid (gabapentin) with glyoxal and cyclohexyl isocyanide or aromatic aldehyde and tertbutyl isocyanide under mild conditions in ethanol have been developed to produce two novel class of N-cyclohexyl-3-(aryl)-3-oxo-2-(3-oxo-2-azaspiro[4.5]decan-2-yl)propanamideins and N-(tert-butyl)-2-(3-oxo-2-azaspiro[4.5]decan-2-yl)-2-arylacetamide derivatives in good to excellent yields. This presents the first report for the intermolecular Ugi three component reaction of gabapentin, glyoxal, and an isocyanide. Also according to the theoretical studies the electron-donating groups increase the strength of intramolecular hydrogen bond and electron-withdrawing groups decrease the strength of intramolecular hydrogen bond.
View MoreWUXI KINGHAN BIO-MEDICAL&CHEMICAL INC.
Contact:13861062998
Address:Room 1316,No.1619 Huishan Avenue,Wuxi,China
website:http://www.finerchem.com
Contact:+86-531-88989536
Address:New Material Industry Park, Jinan Ciyt, China
FUJIAN SHANSHUI CHEMICAL CORP.LTD.
Contact:+86-151-59920036
Address:Jinqiao Gareden, jo@fj-xinyi.com
ABA Chemicals (Shanghai) Limited
Contact:021- 5115 9199-232
Address:Suite 18D, #201 Ningxia Road,
Zhejiang Hoshine Silicon Industry Co., Ltd.
Contact:86-573-89179966
Address:Zhapu Town, Pinghu City, Zhejiang, China
Doi:10.1039/b207840f
(2002)Doi:10.1016/S0960-894X(99)00289-9
(1999)Doi:10.1021/jo020453h
(2003)Doi:10.1016/0008-6215(94)80043-X
(1994)Doi:10.1021/ol034445e
(2003)Doi:10.1021/jo00816a014
(1971)