Synthesis, Table of Contents PAPER© Georg Thieme Verlag Stuttgart ˙ New YorkHighly Efficient Method for C-5 Halogenation of Pyrimidine-Based Nucleosides in Ionic LiquidsVineet Kumar, Jeremy Yap, Andrew Muroyama, Sanjay V. Malhotra*Laboratory of Synthetic Chemistry, SAIC-Frederick Inc., NCI-Frederick, 1050 Boyles Street, Frederick, MD 21702, USAFax: +1(301)8465206; e-Mail: malhotrasa@mail.nih.gov; Recommend Article Abstract Buy Article All articles of this category Abstract A novel, highly efficient, convenient, and benign methodology for C-5 halogenation of pyrimidine-based nucleosides has been developed using N-halosuccinimides as halogenating reagents without using any catalyst in ionic liquid medium. The ionic liquids were successfully recovered and reused for all the reactions. Key words ionic liquids - nucleosides - halogenation Full Text References References <A NAME="RM01709SS-1">1</A> Perigaud C. Gosselin G. Imbach JL. Nucleosides Nucleotides 1992, 11: 903 <A NAME="RM01709SS-2">2</A> De Clercq E. Pure Appl. Chem. 1983, 55: 623 <A NAME="RM01709SS-3">3</A> De Clercq E. Balzarini J. Torrence PF. Mertes MP. Schmidt CL. Shugar D. Barr PJ. Jones AS. Verhelst G. Walker RT. Mol. Pharmacol. 1981, 19: 321 <A NAME="RM01709SS-4">4</A> Van Aershot A. Everaert D. Balzarini J. Augustyns K. Jie L. Janssen G. Peeters O. Blaton N. De Ranter C. De Clercq E. Herdewijn P. J. Med. Chem. 1990, 33: 1833 <A NAME="RM01709SS-5">5</A> Hammersten E. Reichard P. Saluste E. J. Biol. Chem. 1950, 183: 105 <A NAME="RM01709SS-6">6</A> Rose IA. Schweigart BS. J. Biol. Chem. 1953, 202: 635 <A NAME="RM01709SS-7">7</A> Fox L. Dorbersen MJ. Greer S. Antimicrob. Agents Chemother. 1983, 23: 465 <A NAME="RM01709SS-8">8</A> Harki DA. Graci JD. Galarraga JE. Chain WJ. J. Med. Chem. 2006, 49: 6166 <A NAME="RM01709SS-9">9</A> Kobayashi Y. Kumadaki I. Yamamoto K. J. Chem. Soc., Chem. Commun. 1977, 536 <A NAME="RM01709SS-10">10</A> Rahim SG. Duggan MJH. Walker RT. Jones AS. Dyer RL. Balzarini J. De Clercq E. Nucleic Acids Res. 1982, 10: 5285 <A NAME="RM01709SS-11">11</A> Skorobogatyi MV. Ustinov AV. Stepanova IA. Pchelintseva AA. Petrunina AL. Andronova VL. Galegov GA. Malakhov AD. Korshun VA. Org. Biomol. Chem. 2006, 4: 1091 <A NAME="RM01709SS-12">12</A> Cristofoli WA. Wiebe LI. De Clercq E. Andrei G. Snoeck R. Balzarini J. Knaus EE. J. Med. Chem. 2007, 50: 2851 <A NAME="RM01709SS-13">13</A> Mercer JR. Xu LH. Knaus EE. Wiebe LI. J. Med. Chem. 1989, 32: 1289 <A NAME="RM01709SS-14">14</A> Prusoff WH. Holmes WL. Cancer Res. 1953, 13: 221 <A NAME="RM01709SS-15">15</A> Aoyama H. Bull. Chem. Soc. Jpn. 1987, 60: 2073 <A NAME="RM01709SS-16">16</A> Ogino M. Yoshimura Y. Nakazawa A. Saito I. Futimoto K. Org. Lett. 2005, 7: 2853 <A NAME="RM01709SS-17">17</A> Ueda T. Synthesis and Reaction of Pyrimidine Nucleosides, In Chemistry of Nucleosides and Nucleotides Vol. 1: Townsend LB. Plenum Press; New York: 1988. p.1-95 <A NAME="RM01709SS-18">18</A> Levene PA. LaForge FB. Ber. Dtsch. Chem. Ges. 1912, 45: 608 <A NAME="RM01709SS-19">19</A> Srivastava PC. Nagpal KL. Experientia 1970, 26: 220 <A NAME="RM01709SS-20">20</A> Kikugawa K. Kawada I. Ichino M. Chem. Pharm. Bull. 1975, 23: 35 <A NAME="RM01709SS-21">21</A> Ryu EK. Kim JN. Nucleosides Nucleotides 1989, 8: 43 <A NAME="RM01709SS-22">22</A> Frisch DM. Visser DW. J. Am. Chem. Soc. 1959, 81: 1756 <A NAME="RM01709SS-23">23</A> Lipkin D. Howard FB. Nowotny D. Sano M. J. Biol. Chem. 1963, 238: PC2249 <A NAME="RM01709SS-24">24</A> Chang PK. Welch AD. J. Med. Chem. 1963, 6: 428 <A NAME="RM01709SS-25">25</A> Dale RMK. Ward DC. Livingston DC. Martin E. Nucleic Acids Res. 1975, 2: 915 <A NAME="RM01709SS-26">26</A> Paolini L. Petricci E. Corelli F. Botta M. Synthesis 2003, 1039 <A NAME="RM01709SS-27">27</A> Asakura J.-I. Robins MJ. Tetrahedron Lett. 1988, 29: 2855 <A NAME="RM01709SS-28">28</A> Asakura J.-I. Robins MJ. J. Org. Chem. 1990, 55: 4928 <A NAME="RM01709SS-29">29</A> Kumar R. Wiebe LI. Knaus EE. Can. J. Chem. 1994, 72: 2005 <A NAME="RM01709SS-30">30</A> Wasserscheid W. Keim W. Angew. Chem. Int. Ed. 2000, 39: 3772 <A NAME="RM01709SS-31">31</A> Zhao H. Malhotra SV. Aldrichimica Acta 2002, 35: 75 <A NAME="RM01709SS-32">32</A> Prasad AK. Kumar V. Malhotra S. Ravikumar VT. Sanghvi YS. Parmar VS. Bioorg. Med. Chem. 2005, 13: 4467 <A NAME="RM01709SS-33">33</A> Kumar V. Parmar VS. Malhotra SV. Tetrahedron Lett. 2007, 48: 809 <A NAME="RM01709SS-34">34</A> Kumar V. Malhotra S. Bioorg. Med. Chem. Lett. 2008, 18: 5640 <A NAME="RM01709SS-35">35</A> Hunter JH. inventors; US Patent 3651044. ; Chem. Abstr. 1969, 71, 50465 <A NAME="RM01709SS-36">36</A> Youssif S. Mohamed EK. Ahmed FS. Ghoneim AA. Afinidad 2005, 62: 242 <A NAME="RM01709SS-37">37</A> Hwang CH. Park JS. Won JH. Kim JN. Ryu EK. Arch. Pharm. Res. 1992, 15: 69 <A NAME="RM01709SS-38">38</A> Piton N. Mu Y. Stock G. Prisner TF. Schiemann O. Engels JW. Nucleic Acids Res. 2007, 35: 3128