Journal of the Chemical Society. Perkin transactions I p. 1665 - 1670 (1981)
Update date:2022-07-30
Topics:
Barr, Philip J.
Jones, A. Stanley
Verhelst, Gabriel
Walker, Richard T.
Treatment of 5-formyluracil with malonic acid in the presence of piperidine gave (E)-5-(2-carboxyvinyl)uracil which, upon reaction with the appropriate N-halogenosuccinimide, gave (E)-5-(2-bromovinyl)uracil, (E)-5-(2-chlorovinyl)uracil, and (E)-5-(2-iodovinyl)uracil.The last mentioned compound was also obtained by the action of iodine chloride on 5-vinyluracil. 5-(1-Chlorovinyl)uracil upon treatment with bromine gave 5-(2-bromo-1-chlorovinyl)uracil which reacted with sodium methoxide to give 5-bromoethynyluracyl. (E)-5-(2-Bromovinyl)uracil was converted into its trimethylsilyl derivative which was condensed with 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride to give the α- and β-anomers of the blocked deoxyribonucleoside.Removal of the p-toluoyl blocking groups with sodium methoxide afforded (E)-5-(2-bromovinyl)-1-(2-deoxy-α-D-erythro-pentofuranosyl)uracil and (E)-5-(2-bromovinyl)-2'-deoxyuridine.A similar series of reactions gave (E)-5-(2-iodovinyl)-2'-deoxyuridine and 5-(2-bromo-1-chlorovinyl)-2'-deoxyuridine. 5-(1-Chlorovinyl)uracil could be condensed similarly with the blocked sugar derivative to give the α- and β-anomers of the blocked deoxyribonucleoside.Attempted removal of the groups with sodium methoxide gave 2'-deoxy-5-ethynyluridine and mild treatment with methanolic ammonia gave the same product and some 2'-deoxy-5-ethynyl-5'-O-(p-toluoyl)uridine. 5-(1-Chlorovinyl)-2'-deoxyuridine was obtained by the addition of HCl to 2'-deoxy-5-ethynyluridine.Aspects of the elimination reactions of 5-(halogenovinyl)uracil derivatives are discussed.
View MoreNanjing Zelang Medical Technology Co. Ltd
Contact:86-25-83063290/13770714480
Address:Ganjiabian 108# 01 Unit,701-702 room,Yao Hua Street,Qixia District,Nanjing,Jiangsu,China
Shanghai Forever Biotech Co., Ltd.
Contact:+86-21-69734790
Address:Room 5017/5019、5022、5024 of Technology Innovation Centre, No.1155, Gongyuan East Rd, QingPu District, Shanghai China.
Jinan Boss Chemical Industry Co., Ltd.【revoke the business license】
website:http://www.chemboss.com.cn
Contact:+86-531-58591595
Address:No2.Hualong Road, Jinan, China
Chongqing KonAo Health Co.,Ltd
Contact:13687578375
Address:wuhan hubei china
LIAOYANG WANRONG CHEMICALS COMPANY LIMITED
Contact:86-419-2390789
Address:XINLI VILLAGE , DONG NINGWEI COUNTY,TAIZIHE DISTRICT, LIAOYANG , LIAONING
Doi:10.1016/j.cattod.2021.07.025
(2021)Doi:10.1002/jlcr.685
(2003)Doi:10.1039/P19810000582
(1981)Doi:10.1002/ardp.19662990604
(1966)Doi:10.1016/S0040-4039(02)00227-7
(2002)Doi:10.1039/b609908d
(2006)
