Canadian Journal of Chemistry p. 2005 - 2010 (1994)
Update date:2022-08-04
Topics:
Kumar
Wiebe
Knaus
A mild and efficient methodology for the synthesis of 5-halogeno (iodo, bromo, or chloro) uracil nucleosides has been developed. 5-Halo-2'-deoxyuridines 4a-c (84-95%), 5-halouridines 7a-c (45-95%), and 5-haloarabinouridines 8a-c (65-95%) were synthesized in good to excellent yields by the reaction of 2'-deoxyuridine (2), uridine (5) and arabinouridine (6), respectively with iodine monochloride, or N-bromo (or chloro)succinimide, and sodium azide at 25-45°C. These C-5 halogenation reactions proceed via a 5-halo-6-azido-5,6-dihydro intermediate (3), from which HN3 is eliminated, to yield the 5-halogeno uracil nucleoside. The 5-halo-6-azido-5,6-dihydro intermediate products (10a, 10b) could be isolated from the reaction of 3',5'-di-O-acetyl-2'-deoxyuridine (9) with iodine monochloride or N-bromosuccinimide and sodium azide at 0°C. The isolation of 10a, 10b indicates that the C-5 halogenation reaction proceeds via a 5-halo-6-azido-5,6-dihydro intermediate.
View MoreShanghai Kangxin Chemical Co., Ltd
Contact:+86 21 60717227
Address:118,Ganbai Village,Waigang Town,Jiading District,Shanghai
Wuxi Pharma-Trading Import & Export Co.,Ltd.
Contact:+86-510-82304590 82716390
Address:Room 523,Youzu Alliance Building,No.88 Renmin Zhonglu,Wuxi,Jiangsu,China
Suzhou Tianma Specialty Chemicals Co.,Ltd
Contact:+86-512-68090577
Address:#199, Huayuan Rd, Mudu, Suzhou, Jiangsu, CHINA
Qingdao Pana-Life Biochem Co.,Ltd.
Contact:86-532-87683902
Address:No.967 Dalao Road, Licang Zone, Qingdao City,Shandong, China 266021
HANGZHOU GOPHER CHEM-TECH CO.,LTD
Contact:86-189-58111780
Address:Da Cheng Ming Zuo Plaza,Xiaoshan District
Doi:10.1080/10610278.2018.1494275
(2018)Doi:10.1021/ja01329a040
(1933)Doi:10.1021/ol016960n
(2001)Doi:10.1007/BF00846201
()Doi:10.1016/S0022-328X(00)82916-2
(1972)Doi:10.1021/j100243a036
(1983)