Citation: Jian-Jun Li, Xing-Xing Gui. L-ProT catalyzed highly regioselective N-alkoxyalkylation of purine rings with vinyl ethers[J]. Chinese Chemical Letters, ;2014, 25(10): 1341-1345. doi: 10.1016/j.cclet.2014.04.023 shu

L-ProT catalyzed highly regioselective N-alkoxyalkylation of purine rings with vinyl ethers

Jian-Jun Li ^, ,
Xing-Xing Gui

1.
Key Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, China

Corresponding author: Jian-Jun Li,
Received Date: 17 February 2014
Available Online: 8 April 2014
Fund Project: We are grateful to the Natural Science Foundation of Zhejiang Province (No. LY13B020015) (No. LY13B020015)Zhejiang Key Innovation Team of Green Pharmaceutical Technology (No. 2012R10043-07) for financial support. (No. 2012R10043-07)

An efficient and regioselective synthesis of N-9 alkoxyalkylated purine nucleoside derivatives was achieved via the N-alkoxyalkylation of purine rings with vinyl ethers catalyzed by _L-ProT. The advantages of this protocol include good to excellent yield, mild reaction condition, and simple manipulation. A plausible mechanism for the transformation was given.
- L-Proline triflate,
- Regioselectivity,
- Purine,
- Vinyl ether,
- Addition reaction
1. [1]
  [1] H. Rosemeyer, The chemodiversity of purine as a constituent of natural products, Chem. Biodivers 1 (2004) 361-401.
2. [2]
  [2] H.B. Xu, R.F. Ye, S.Y. Yang, R. Li, X. Yang, Electrochemical DNA nano-biosensor for the detection of genotoxins in water samples, Chin. Chem. Lett. 25 (2014) 29-34.
3. [3]
  [3] E.D. Clercq, Antiviral drugs: current state of the art, J. Clin. Virol. 22 (2001) 73-89.
4. [4]
  [4] P. Lu, S.H. Jiang, J.X. Liu, Y.S. She, R.Y. Ji, Design, synthesis and anti-HBV activity of novel bis(trifluoroethyl)phosphonomethyl ether derivatives of acyclovir, Chin. Chem. Lett. 20 (2009) 507-510.
5. [5]
  [5] W.B. Parker, Enzymology of purine and pyrimidine antimetabolites used in the treatment of cancer, Chem. Rev. 109 (2009) 2880-2893.
6. [6]
  [6] E. de Clercq, Ten paths to the discovery of antivirally active nucleoside and nucleotide analogues, Nucleosides Nucleotides Nucleic Acids 31 (2012) 339-352.
7. [7]
  [7] U. Diederichsen, D. Weicherding, N. Diezemann, Side chain homologation of alanyl peptide nucleic acids: pairing selectivity and stacking, Org. Biomol. Chem. 3 (2005) 1058-1066.
8. [8]
  [8] M. Kitamatsu, A. Takahashi, T. Ohtsuki, M. Sisido, Synthesis of pyrrolidine-based oxy-peptide nucleic acids carrying four types of nucleobases and their transport into cytoplasm, Tetrahedron 66 (2010) 9659-9666.
9. [9]
  [9] N.F. Zakirova, A.V. Shipitsyn, E.F. Belanov, M.V. Jasko, A new approach to the synthesis of optically active alkylated adenine derivatives, Bioorg. Med. Chem. Lett. 14 (2004) 3357-3360.
10. [10]
  [10] M. Gandelman, E.N. Jacobsen, Highly enantioselective catalytic conjugate addition of N-heterocycles to α,β-unsaturated ketones and imides, Angew. Chem. Int. Ed. 44 (2005) 2393-2397.
11. [11]
  [11] E.P. Lira, C.W. Huffman, Some Michael-type reactions with adenine, J. Org. Chem. 31 (1965) 2188-2191.
12. [12]
  [12] H. Wu, Z.Q. Tian, L.L. Zhang, Y.D. Huang, Y.M. Wang, Organocatalytic enantioselective aza-Michael addition of purine bases to α,β-unsaturated ketones, Adv. Synth. Catal. 354 (2012) 2977-2984.
13. [13]
  [13] M.R. Peel, D.D. Sternbach, M.R. Johnson, A short, enantioselective synthesis of the carbocyclic nucleoside carbovir, J. Org. Chem. 56 (1991) 4990-4993.
14. [14]
  [14] T. Borrmann, A. Abdelrahman, R. Volpini, et al., Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family, J. Med. Chem. 52 (2009) 5974-5989.
15. [15]
  [15] D. Singh, M.J. Wani, A. Kumar, A simple solution to the age old problem of regioselective functionalization of guanine: first practical synthesis of acyclic N⁹-and/or N⁷-guanine nucleosides starting from N²,N⁹-diacetylguanine, J. Org. Chem. 64 (1999) 4665-4668.
16. [16]
  [16] T. Funatomi, K. Wakasugi, T. Misaki, Y. Tanabe, Pentafluorophenylammonium triflate (PFPAT): an efficient, practical, and cost-effective catalyst for esterification, thioesterification, transesterification, and macrolactone formation, Green Chem. 8 (2006) 1022-1027.
17. [17]
  [17] B. Karimi, M. Ghoreishi-Nezhad, Highly chemoselective acetalization of carbonyl compounds catalyzed by a novel recyclable ammonium triflate-functionalized silica, J. Mol. Catal. A: Chem. 277 (2007) 262-265.
18. [18]
  [18] L. Mercs, G. Pozzi, S. Quici, Efficient condensation of carboxylic acids with alcohols catalyzed by fluorous ammonium triflates, Tetrahedron Lett. 48 (2007) 3053-3056.
19. [19]
  [19] N. Montazeri, S. Mahjoob, Highly efficient and easy synthesis of 2,4,6-triarylpyr-idines catalyzed by pentafluorophenylammonium triflate (PFPAT) as a new recyclable solid acid catalyst in solvent-free conditions, Chin. Chem. Lett. 23 (2012) 419-422.
20. [20]
  [20] J.J. Li, L.M. Lu, W.K. Su, A new strategy for the synthesis of benzoxanthenes catalyzed by proline triflate in water, Tetrahedron Lett. 51 (2010) 2434-2437.
21. [21]
  [21] J.J. Li, P. He, C.M. Yu, DPAT-catalyzed one-pot regioselective synthesis of polysubstituted pyridines and 1,4-dihydropyridines, Tetrahedron 68 (2012) 4138-4144.
22. [22]
  [22] K. Groebke, J. Hunziker, W. Fraser, et al., Chemistry of a-amino nitriles. Part 9. Why pentose-and not hexose-nucleic acids? Part 5. Purine-purine pairing in homo-DNA. Guanine, isoguanine, 2,6-diaminopurine, and xanthine, Helv. Chim. Acta 81 (1998) 375-474.
23. [23]
  [23] M. Miyaki, B. Shimizu, N→N Alkyl and glycosyl migration of purines and pyrimidines. II. Glycosyl migration of 3-glycosyl-N⁶-acyladenine derivatives, Chem. Pharm. Bull. 18 (1970) 732-740.
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