A. Sniady, M. Morreale, K. Wheeler
Jul 1, 2008
Citations
0
Influential Citations
46
Citations
Journal
European Journal of Organic Chemistry
Abstract
The 5-endo-dig chlorocyclization of 1,4-disubstituted alk-3-yn-1-ones (propargylic ketones) with the use of trichloro-s-triazinetrione (trichloroisocyanuric acid, TCCA; 0.4 equiv.) in toluene, at room temperature, in the absence of base, provides 2,5-disubstituted 3-chlorofurans in high yields (79–96 %). The reaction can be accomplished by using commercially available swimming pool sanitizer. Selected 3-chlorofuran was validated as a substrate for Suzuki–Miyaura coupling. In a similar manner, chlorocyclization of 5-alkynyl-2′-deoxyuridines produces 5-chlorofuropyrimidine nucleosides (76–83 %), which are analogues of potent anitviral agents. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)