A novel synthesis of 1,5-disubstituted fluorinated tetrazoles from 1,1-difluoroazides

Tetrahedron Letters

Volumn 51, Issue 32, 2010, Pages 4205-4207

  Polivanova, Anna G ^a   Shkavrov, Sergey V ^b   Churakov, Andrei V ^c   Lermontov, Anatoly S ^c   Lermontov, Sergey A ^d  

^a MENDELEEV UNIVERSITY OF CHEMICAL TECHNOLOGY OF RUSSIA   (Russian Federation)

^b Chemical Diversity Research Institute   (Russian Federation)

^c KURNAKOV INSTITUTE OF GENERAL AND INORGANIC CHEMISTRY   (Russian Federation)

^d INSTITUTE OF PHYSIOLOGICALLY ACTIVE COMPOUNDS   (Russian Federation)

Author keywords

1,5 Substituted fluorinated tetrazoles; Difluoroazides; Fluorine nucleophilic substitution

Indexed keywords

AMINE; AZIDE; TETRAZOLE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS;

EID: 77955309384     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.06.016     Document Type: Article

References (35)

1. E.G. Gross, and R.M. Featherstone J. Pharm. Exp. Ther. 87 1946 299
2. D.D. Beusen, J. Zabrocki, U. Slomczynska, R.D. Head, J.L.-F. Kao, and G.R. Marshall Biopolymers 36 1995 181
3. L.V. Myznikov, A. Hrabalek, and G.I. Koldobskii Chem. Heterocycl. Compd. 43 2007 1
4. D.W. Nelson, R.J. Gregg, M.E. Kort, A. Perez-Medrano, E.A. Voight, Y. Wang, G. Grayson, M.T. Namovic, D.L. Donnelly-Roberts, W. Niforatos, P. Honore, M.F. Jarvis, C.R. Faltynek, and W.A. Carroll J. Med. Chem. 49 2006 3659
5. P. Srihari, P. Dutta, R. Srinivasa Rao, J.S. Yadav, S. Chandrasekhar, P. Thombare, J. Mohapatra, A. Chatterjee, and M.R. Jain Bioorg. Med. Chem. Lett. 19 2009 5569
6. G. Ortar, A.S. Moriello, M.G. Cascio, L. De Petrocellis, A. Ligresti, E. Morera, M. Nalli, and V. Di Marzo Bioorg. Med. Chem. Lett. 18 2008 2820
7. L.M.T. Frija, I.V. Khmelinskii, and M.L.S. Cristiano Tetrahedron Lett. 46 2005 6757
8. P. Jankowski, K. Plesniak, and J. Wicha Org. Lett. 5 2003 2789
9. D. Potts, P.J. Stevenson, and N. Thompson Tetrahedron Lett. 41 2000 275
10. G.I. Koldobskii, and V.A. Ostrovskii Russ. Chem. Rev. 63 1994 797
11. R.N. Butler A.R. Katritzky, C.W. Rees, Comprehensive Heterocyclic Chemistry Vol. 5 1984 Pergamon Oxford, UK 791 838
12. A.R. Katritzky, C. Cai, and N.K. Meher Synthesis 2007 1204
13. S. Hajra, D. Sinha, and M. Bhowmick J. Org. Chem. 72 2007 1852
14. T. Yue, M.-X. Wang, D.-X. Wang, and J. Zhu Angew. Chem., Int. Ed. 47 2008 9454
15. P.N. Gaponik, V.P. Karavai, and Y.V. Grigor'ev Chem. Heterocycl. Compd. 21 1985 1255
16. W.-K. Su, Z. Hong, W.-G. Shan, and X.-X. Zhang Eur. J. Org. Chem. 2006 2723
17. W.R. Carpenter J. Org. Chem. 27 1962 2085
18. W.P. Norris J. Org. Chem. 27 1962 3248
19. K.E. Peterman, and J.M. Sheeve J. Fluorine Chem. 6 1975 83
20. A.R. Bailey, and R.E. Banks J. Fluorine Chem. 24 1984 117
21. C.C. Kotoris, M.-J. Chen, and S.D. Taylor J. Org. Chem. 63 1998 8052
22. M.-J. Chen, and S.D. Taylor Tetrahedron Lett. 40 1999 4149
23. F.M.D. Ismail J. Fluorine Chem. 118 2002 27
24. W.K. Hagmann J. Med. Chem. 51 2008 4359
25. I.L. Knunyants, and E.G. Bykhovskaya Dokl. Akad. Nauk. SSSR 131 1960 1338
26. R.E. Banks, and G.J. Moore J. Chem. Soc. 24 1966 2304
27. C.G. Krespan J. Org. Chem. 51 1986 332
28. C.G. Krespan J. Am. Chem. Soc. 106 1984 5544
29. A. Haas, M. Spitzer, and M. Lieb Chem. Ber. 121 1988 1329
30. S.A. Lermontov, I.I. Sukhojenko, A.V. Popov, A.N. Pushin, I.V. Martynov, N.S. Zefirov, and P.J. Stang Heteroatom Chem. 4 1993 579
31. C.S. Cleaver, and C.G. Krespan J. Am. Chem. Soc. 87 1965 3716
32. S.A. Lermontov, S.V. Shkavrov, and A.N. Pushin J. Fluorine Chem. 105 2000 141
33. S.A. Lermontov, S.V. Shkavrov, A.N. Pushin, and V.V. Tkachev Russ. J. Gen. Chem. 72 2002 1289
34. N.N. Yarovenko, and M.A. Raksha Zh. Obshch. Khim. 29 1959 2159
35. A. Takaoko, H. Iwakiri, and N. Ishikawa Bull. Chem. Soc. Jpn. 52 1979 3377