Journal of the Chemical Society. Perkin transactions I p. 2541 - 2546 (1988)
Update date:2022-07-30
Topics:
Mackenzie, Grahame
Wilson, Hilary A.
Shaw, Gordon
Ewing, David
Treatment of ethyl-5-amino-1-benzylimidazole-4-carboxylate with butyl-lithium and methyl iodide gave the 5-N-methylamino derivative (4b) and the 3-methiodide (5) whereas ethyl-5-amino-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)imidazole-4-carboxylate gave both the 5-N-methylamino (6b) and 2-methyl (6d) derivatives.Ethyl 5-amino-1-benzylimidazole-4-carboxylate with acetic anhydride or acetyl chloride gave various products, according to the conditions, including the 5-N-mono- and -N,N-di-acetylamino derivatives (4d) and (4c), respectively, and N,N'-dibenzyloxamide (9).The oxamide also arose from treatment of the imidazole (4a) with formaldehyde. 3-Cyanopropanimidate with ethyl α-amino-α-cyano acetate followed by benzylamine or 2,3-O-isopropylidene-D-ribosylamine afforded ethyl 5-amino-1-benzyl-2-(2-cyanoethyl)imidazole-4-carboxylate and ethyl 5-amino-1-(2,3-O-isopropylidene-α- and β-D-ribofuranosyl)imidazole-4-carboxylates, respectively.Ethyl 5-amino-(2,3-O-isopropylidene-β-D-ribofuranosyl)-2-ethoxycarbonylethylimidazole-4-carboxylate and the corresponding 2-ethoxyethyl nucleoside (6i) were similarly prepared.Oxidation of ethyl 5-amino-2-methylimidazole-4-carboxylate with N-chlorosuccinimide and potassium hydroxide led to ethyl 5-amino-1-benzyl-2-formylimidazole-4-carboxylate and oxidation of the protected 2-ethoxycarbonylethyl nucleoside (6j) with selenium dioxide produced the urea derivative (6l).
View MoreTianjin Emulsion Science&Technology Development Co.,Ltd
Contact:13901380442
Address:Vake Garden New Town New Yi Bai Road Beichen District Tianjin,China
website:http://www.lonwinchem.com
Contact:Tel: 86-21-59858395
Address:No#966,Huaxu Road,Shanghai 201702,P.R.China
Changzhou Welton Chemical Co., Ltd,
Contact:0086-519-85910828,85920537,85912897
Address:No.8 Jinlong Road, Binjiang Park, Changzhou, Jiangsu, China.
Contact:+86+21-58956006 15800617331
Address:402 Room, 150# Cailun Road, Zhangjiang high tech park, Shanghai
Contact:+86-571-86217390
Address:No.567 Dengcai Street,Sandun,Westlake District,Hangzhou310030,Zhejiang,China.
Doi:10.1039/c8md00582f
(2019)Doi:10.1002/hlca.19880710514
(1988)Doi:10.1016/j.saa.2012.01.035
(2012)Doi:10.1021/acs.jmedchem.7b00785
(2017)Doi:10.1016/j.tetlet.2009.07.130
(2009)Doi:10.1016/j.bmc.2009.07.027
(2009)
