1055900-77-0Relevant articles and documents
Room-temperature electrophilic 5-endo-dig chlorocyclization of alk-3-yn-1-ones with the use of pool sanitizer: Synthesis of 3-chlorofurans and 5-chlorofuropyrimidine nucleosides
Sniady, Adam,Morreale, Marco S.,Wheeler, Kraig A.,Dembinski, Roman
experimental part, p. 3449 - 3452 (2009/04/10)
The 5-endo-dig chlorocyclization of 1,4-disubstituted alk-3-yn-1-ones (propargylic ketones) with the use of trichloro-striazinetrione (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, 2008.