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Short Communication
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
Article first published online: 30 MAY 2008
DOI: 10.1002/ejoc.200800397
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Sniady, A., Morreale, M. S., Wheeler, K. A. and Dembinski, R. (2008), 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. Eur. J. Org. Chem., 2008: 3449–3452. doi: 10.1002/ejoc.200800397
Publication History
- Issue published online: 23 JUN 2008
- Article first published online: 30 MAY 2008
- Manuscript Received: 31 JAN 2008
Funded by
- Petroleum Research Fund administered by the American Chemical Society. Grant Number: ACS-PRF#46094
- National Institute of Health (NIH). Grant Number: (CA111329
- Oakland University and its Research Excellence Program in Biotechnology
Keywords:
- Alkynes;
- C–C coupling;
- Cyclizations;
- Halogenation;
- Heterocycles;
- Ketones;
- Nucleosides;
- Trichloroisocyanuric acid
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)