Highly efficient protocol for one-pot N-alkylation of nucleobases using alcohols in bmim[Br]: a rapid route to access acyclic nucleosides

详细信息    查看全文

• 作者：Mohammad Navid Soltani Rad ; Somayeh Behrouz…
• 关键词：Acyclic nucleoside ; Alcohol ; Ionic liquids ; Nucleobase ; One ; pot N ; alkylation
• 刊名：Journal of the Iranian Chemical Society
• 出版年：2015
• 出版时间：September 2015
• 年：2015
• 卷：12
• 期：9
• 页码：1603-1612
• 全文大小：618 KB
• 参考文献：1.E. De Clercq, in Advances in Antiviral Drug Design, vol. 1, ed. by N.G Johnsson (JAI, Greenwich, 1993), pp. 88鈥?64
  2.C.K. Chu, S.J. Cutler, J. Heterocycl. Chem. 23, 289 (1986). doi:10.鈥?002/鈥媕het.鈥?570230201 View Article
  3.T. Pathak, Chem. Rev 102, 1623 (2002). doi:10.鈥?021/鈥媍r0104532 View Article
  4.E. Ichikawa, K. Kato, Synthesis 1 (2002). doi:10.鈥?055/鈥媠-2002-19289
  5.L.A. Agrofoglio, I. Gillaizeau, Y. Saito, Chem. Rev. 103, 1875 (2003). doi:10.鈥?021/鈥媍r010374q View Article
  6.D.M. Huryn, M. Okabe, Chem. Rev. 92, 1745 (1992). doi:10.鈥?021/鈥媍r00016a004 View Article
  7.M. Yokoyamma, A. Momotake, Synthesis 1541 (1999). doi:10.鈥?055/鈥媠-1999-3559
  8.M. Yokoyamma, Synthesis 1637 (2000). doi:10.鈥?055/鈥媠-2000-8194
  9.A. Khalafi-Nezhad, M.N. Soltani Rad, A. Khoshnood, Synthesis 583 (2004). doi:10.鈥?055/鈥媠-2004-815968
  10.J.L. Wong, D.S. Fuchs, J. Org. Chem. 36, 848 (1971). doi:10.鈥?021/鈥媕o00805a028 View Article
  11.A. Gambacorta, M.E. Farah, D. Tofani, Tetrahedron 55, 12615 (1999). doi:10.鈥?016/鈥婼0040-4020(99)00736-X View Article
  12.N.G. Kundu, S. Sikdar, R.P. Hertzberg, S.A. Schmitz, S.G. Khatri, J. Chem. Soc. 1, 1295 (1985). doi:10.鈥?039/鈥婸19850001295
  13.J.W. Rigoli, M.E. 脴stergaard, K.M. Canady, D.C. Guenther, P.J. Hrdlicka, Tetrahedron Lett. 50, 1751 (2009). doi:10.鈥?016/鈥媕.鈥媡etlet.鈥?009.鈥?1.鈥?47 View Article
  14.A. Houlton, C.J. Isaac, A.E. Gibson, B.R. Horrocks, W. Clegg, M.R.J. Elsegood, J. Chem. Soc., Dalton Trans. 3229 (1999). doi:10.鈥?039/鈥婣905168F
  15.M.F. Jacobsen, M.M. Knudsen, K.V. Gothelf, J. Org. Chem. 71, 9183 (2006). doi:10.鈥?021/鈥媕o061694i View Article
  16.J. March, Advanced organic chemistry, 7th edn. (Wiley, Singapore, 2013)
  17.H. Bipp, H. Kieczka, Formamides, in Ullmann鈥檚 encyclopedia of industrial chemistry, (Wiley-VCH, Weinheim, 2005)
  18.A. Gescher, Chem. Res. Toxicol. 6, 245 (1993). doi:10.鈥?021/鈥媡x00033a001 View Article
  19. http://鈥媤ww.鈥媤ho.鈥媔nt/鈥媔pcs/鈥媝ublications/鈥媍icad/鈥媏n/鈥媍icad31.鈥媝df (accessed November 2014)
  20.A. Khalafi-Nezhad, M.N. Soltani Rad, A.A. Moosavi-Movahedi, M. Kosari, Helv. Chim. Acta 90, 730 (2007). doi:10.鈥?002/鈥媓lca.鈥?00790073 View Article
  21.M.R. Harnden, R.L. Jarvest, Tetrahedron Lett. 26, 4265 (1985). doi:10.鈥?016/鈥婼0040-4039(00)99010-5 View Article
  22.M.A. Biamonte, J. Shi, K. Hong, D.C. Hurst, L. Zhang, J. Fan, D.J. Busch, P.L. Karjian, A.A. Maldonado, J.L. Sensintaffar, Y.-C. Yang, A. Kamal, R.E. Lough, K. Lundgren, F.J. Burrows, G.A. Timony, M.F. Boehm, S.R. Kasibhatla, J. Med. Chem. 49, 817 (2006). doi:10.鈥?021/鈥媕m0503087 View Article
  23.A. Manikowski, A. Verri, A. Lossani, B.M. Gebhardt, J. Gambino, F. Focher, S. Spadari, G.E. Wright, J. Med. Chem. 48, 3919 (2005). doi:10.鈥?021/鈥媕m049059x View Article
  24.J.M. Beal, J.H. Block, Wilson & Gisvold鈥檚 Textbook of Organic Medicinal and Pharmaceutical Chemistry, 12th edn. (Lippincott Williams & Wilkins, 2011)
  25.M.N. Soltani Rad, S. Behrouz, H. Najafi, Synthesis 1380 (2014). doi:10.鈥?055/鈥媠-0033-1341026
  26.O. Mitsunobu, Synthesis 1 (1981). doi:10.鈥?055/鈥媠-1981-29317
  27.S.F. Martin, J.A. Dodge, Tetrahedron Lett. 32, 3017 (1991). doi:10.鈥?016/鈥?040-4039(91)80675-V View Article
  28.D.L. Hughes, Org. Prep. Proced. Int. 28, 127 (1996). doi:10.鈥?080/鈥?030494960935651鈥? View Article
  29.C. Hubert, C. Alexandre, A.-M. Aubertin, F. Huet, Tetrahedron 59, 3127 (2003). doi:10.鈥?016/鈥婼0040-4020(03)00373-9 View Article
  30.K.R. Kim, H.R. Moon, A.-Y. Park, M.W. Chun, L.S. Jeong, Bioorg. Med. Chem. 15, 227 (2007). doi:10.鈥?016/鈥媕.鈥媌mc.鈥?006.鈥?9.鈥?66 View Article
  31.M. Yang, J. Zhou, S.W. Schneller, Tetrahedron 62, 1295 (2006). doi:10.鈥?016/鈥媕.鈥媡et.鈥?005.鈥?0.鈥?52 View Article
  32.P. Wasserscheid, T. Welton, Ionic liquids in synthesis (Wiley, Weinheim, 2003)
  33.T. Welton, Chem. Rev. 99, 2071 (1999). doi:10.鈥?021/鈥媍r980032t View Article
  34.D.G. Gu, S.J. Ji, Z.Q. Jiang, M.F. Zhou, T.P. Loh, Synlett 959 (2005). doi:10.鈥?055/鈥媠-2005-865194
  35.M.N. Soltani Rad, S. Behrouz, Mol. Divers. 17, 9 (2013). doi:10.鈥?007/鈥媠11030-012-9412-z View Article
  36.A. Kamal, G. Chouhan, Tetrahedron Lett. 46, 1489 (2005). doi:10.鈥?016/鈥媕.鈥媡etlet.鈥?005.鈥?1.鈥?40 View Article
  37.K. Qiao, C. Yakoyama, Chem. Lett. 33, 472 (2004). doi:10.鈥?246/鈥媍l.鈥?004.鈥?72 View Article
  38.W. Sun, C.G. Xia, H.W. Wang, Tetrahedron Lett. 44, 2409 (2003). doi:10.鈥?016/鈥婼0040-4039(03)00185-0 View Article
  39.W. Bao, Z. Wang, Green Chem. 8, 1028 (2006). doi:10.鈥?039/鈥媌604096a View Article
  40.S. Chowdhury, R.S. Mohan, J.L. Scott, Tetrahedron 63, 2363 (2007). doi:10.鈥?016/鈥媕.鈥媡et.鈥?006.鈥?1.鈥?01 View Article
  41.D. Zhao, M. Wu, Y. Kou, E. Min, Catal. Today 74, 157 (2002). doi:10.鈥?016/鈥婼0920-5861(01)00541-7 View Article
  42.A.R. Hajipour, F.J. Rafiee, Iran Chem. Soc. 6, 647 (2009). doi:10.鈥?007/鈥婤F03246155 View Article
  43.H. Xue, R. Verma, J.M. Shreeve, J. Fluor. Chem. 127, 159 (2006). doi:10.鈥?016/鈥媕.鈥媕fluchem.鈥?005.鈥?1.鈥?07 View Article
  44.J. Dupont, R.F. Souza, P.A.Z. de Suarez, Chem. Rev. 102, 3667 (2002). doi:10.鈥?021/鈥媍r010338r View Article
  45.S. Keskin, D. Kayrak-Talay, U. Akman, 脰. Horta莽su, J. Supercrit. Fluids 43, 150 (2007). doi:10.鈥?016/鈥媕.鈥媠upflu.鈥?007.鈥?5.鈥?13 View Article
  46.T. Erdmenger, J. Vitz, F. Wiesbrock, U.S. Schubert, J. Mater. Chem. 18, 5267 (2008). doi:10.鈥?039/鈥媌807119e View Article
  47.H.F.D. Almeida, M.G. Freire, A.M. Fernandes, J.A. Lopes-da-Silva, P. Morgado, K. Shimizu, E.J.M. Filipe, J.N.C. Lopes, L.M.N.B.F. Santos, J.A.P. Coutinho, Langmuir 30, 6408 (2014). doi:10.鈥?021/鈥媗a501308q View Article
  48.S. Li, J.L. Ba帽uelos, J.C. Guo, L. Anovitz, G. Rother, R.W. Shaw, P.C. Hillesheim, S. Dai, G.A. Baker, P.T. Cummings, J. Phys. Chem. Lett. 3, 125 (2012). doi:10.鈥?021/鈥媕z2013209 View Article
  49.A. Monopoli, P. Cotugno, M. Cortese, C.D. Calvano, F. Ciminale, A. Nacci, Eur. J. Org. Chem. 2012, 3105 (2012). doi:10.鈥?002/鈥媏joc.鈥?01200202 View Article
  50.M.N. Soltani Rad, A. Khalafi-Nezhad, S. Behrouz, M.A. Faghihi, A. Zare, A. Parhami, Tetrahedron 64, 1778 (2008). doi:10.鈥?016/鈥媕.鈥媡et.鈥?007.鈥?1.鈥?01 View Article
  51.M.N. Soltani Rad, A. Khalafi-Nezhad, S. Behrouz, Z. Asrari, M. Behrouz, Z. Amini, Synthesis 3067 (2009). doi:10.鈥?055/鈥媠-0029-1216887
  52.R.P. Swatloski, J.D. Holbrey, R.D. Rogers, Green Chem. 5, 361 (2003). doi:10.鈥?039/鈥媌304400a View Article
  53.P.J. Dyson, T.J. Geldbach, Metal catalysed reactions in ionic liquids. Catalysis by metal complexes 29, (Springer Science & Business, Geldbach, 2005), p. 27
  54.R. Kalb, Metathesis of a quaternary ammonium, phosphonium or sulfonium cation forming a salt of hydrogencarbonate, carbonate, monoalkylcarbonate or monoarylcarbonate; storage stablility, U. S. Patent 8075803B2, 13 Dec 2011
  
• 作者单位：Mohammad Navid Soltani Rad (1)
  Somayeh Behrouz (1)
  Elham Zarenezhad (2)
  Narjes Kaviani (1)
  
  1. Medicinal Chemistry Research Laboratory, Department of Chemistry, Shiraz University of Technology, 71555-313, Shiraz, Iran
  2. Department of Chemistry, Islamic Azad University, Yazd Branch, Yazd, Iran
  
• 刊物主题：Analytical Chemistry; Inorganic Chemistry; Physical Chemistry; Biochemistry, general; Organic Chemistry;
• 出版者：Springer Berlin Heidelberg
• ISSN：1735-2428

文摘

Highly efficient protocol for one-pot N-alkylation of nucleobases using alcohol in ionic liquid media as a straightforward route to access acyclic nucleoside was described. In this protocol purine, pyrimidine as well as azole derivatives underwent the N-alkylation reaction with primary or secondary alcohols using TsCl/TEA/K2CO3 in bmim[Br] to afford the products in good-to-excellent yields. The influence of factors in this method including the type of ionic liquid, base and sulfonating agents was discussed. The current method showed an appropriate selectivity in reaction with primary alcohols in comparison with secondary alcohols. This protocol is mild, safe and easy to apply; moreover, it is quite compatible with eco-friendly and green chemistry protocols, since the exploitation of toxic and hazardous materials such as DMF and alkyl halides has been prevented.