New functionalization at the 5-position of uracils by selenenylation

✍ Scribed by Yong Hae Kim; Chun Ho Lee; Dong Hoon Lee

• Book ID: 102846571
• Publisher: John Wiley and Sons
• Year: 1993
• Tongue: English
• Weight: 532 KB
• Volume: 4
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.520040509

✦ Synopsis

Abstract

Electrophilic substitution of phenylselenenyl chloride at the 5‐position of uracils in the presence of silver reagents, such as Ag~2~O, AgBF~4~, or CF~3~CO~2~Ag, afforded the corresponding 5‐phenylselenenyluracils in excellent yields. 1,3‐Dimethyl‐5‐phenylselenenyluracil(2a), 5‐phenylselenenyl‐(2′,3′,5′‐tri‐O‐acetyl)uridine(2b), 5‐phenylselenoxyl‐1,3‐dimethyluracil(3a) and 5‐phenylselenoxyl‐(2′,3′,5′‐tri‐O‐acetyl)uridine(3b) were used for various transformations at C‐5 or C‐6 of pyrimidine bases via nucleophilic substitution, a free radical process, and a Michael‐type addition utilizing the unique properties of organo‐seleno groups located on C‐5 of pyrimidine bases.