Cycloaddition reactions of glycine imine anions to phenylazocarboxylic esters - A new access to 1,3,5-trisubstituted 1,2,4-triazoles

Tetrahedron

Volumn 71, Issue 25, 2015, Pages 4282-4295

  Lasch, Roman ^a   Heinrich, Markus R ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

1,2,4 Triazoles; Azo compounds; Azocarboxylic esters; Cycloaddition; Glycine imines

Indexed keywords

ANION; AZOBENZENE DERIVATIVE; GLYCINE; GLYCINE IMINE; IMINE; PHENYLAZOCARBOXYLATE ESTER; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CYCLOADDITION; DRUG MIXTURE; ELECTROPHILICITY; HYDROLYSIS; ISOMER; ONE POT SYNTHESIS; OXIDATION; PRIORITY JOURNAL; STEREOSPECIFICITY;

EID: 84930180882     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2015.04.078     Document Type: Article

References (63)

1. Reviews on uses preparation of 1,2,4-triazoles
2. A. Al-Masoudi, Y.A. Al-Soud, N.J. Al-Salihi, and N.A. Al-Masoudi Chem. Heterocycl. Compd. 42 2006 1377
3. K. Shalini, N. Kumar, S. Drabu, and P.K. Sharma Beilstein J. Org. Chem. 7 2011 668
4. M.H. Klingele, and S. Brooker Coord. Chem. Rev. 241 2003 119
5. Rilmazafone: M. Koike, R. Norikuram, K. Iwatani, K. Sugeno, S. Takahashi, and Y. Nakagawa Xenobiotika 18 1988 257
6. Flupoxam: T. Shida, H. Arabori, T. Watanabe, Y. Kubota, I. Ichinose, Y. Kanda, S. Yamazaki, and H. Shinkawa EP0282303A1, 1988 Chem. Abstr. 110 1989 95247p
7. K.T. Potts Chem. Rev. 61 1961 87
8. For a review article see: A. Moulin, M. Bibian, A.-L. Blayo, S. El Habnouni, J. Martinez, and J.-A. Fehrentz Chem. Rev. 110 2010 1809
9. For recent examples, see
10. V. Siddaiah, G.M. Basha, R. Srinuvasarao, and S.K. Yadav Catal. Lett. 141 2011 1511
11. M. Bibian, A.-L. Blayo, A. Moulin, J. Martinez, and J.-A. Fehrentz Tetrahedron Lett. 51 2010 2660
12. O. Bekircan, and H. Bektas Molecules 11 2006 469 Milcent, R.; Redeuilh, C. J. Heterocycl. Chem. 1977, 14, 53
13. G.M. Castanedo, P.S. Seng, N. Blaquiere, S. Trapp, and S.T. Staben J. Org. Chem. 76 2011 1177
14. J. Lee, M. Hong, Y. Jung, E.J. Cho, and H. Rhee Tetrahedron 68 2012 2045
15. R. Xie, X. Liu, C. Mai, and Z. Liu Int. J. Org. Chem. 3 2013 35
16. M.J. Stocks, D.R. Cheshire, and R. Reynolds Org. Lett. 6 2004 2969
17. For recent syntheses of 1,3-, 1,5- and 3,5-disubstituted 1,2,4-triazoles, see: 1,3
18. A. Tam, I.S. Armstrong, and T.E. La Cruz Org. Lett. 15 2013 3586 1,5
19. Y. Xu, M. McLaughlin, E.N. Bolten, and R.A. Reamer J. Org. Chem. 75 2010 8666 3,5
20. S. Ueda, and H. Nagasawa J. Am. Chem. Soc. 131 2009 15080
21. For a recently developed four-component reaction to access triazoles via acylhydrazones, see
22. S.T. Staben, and N. Blaquiere Angew. Chem., Int. Ed. 49 2010 325 For other condensation reactions for 1,2,4-triazols, see
23. R. Heckdorn Helv. Chim. Acta 70 1987 2118
24. W.-C. Tseng, L.-Y. Wang, T.-S. Wu, and F.F. Wong Tetrahedron 67 2011 5339
25. L.-Y. Wang, H.J. Tsai, H.-Y. Lin, K. Kaneko, F.-Y. Cheng, H.-S. Shih, F.F. Wong, and J.-J. Huang RSC Adv. 4 2014 14215
26. L.-Y. Wang, W.-C. Tseng, T.-S. Wu, K. Kaneko, H. Takayama, M. Kimura, W.-C. Yang, J.B. Wu, S.-H. Juang, and F.F. Wong Bioorg. Med. Chem. Lett. 21 2011 5358
27. For a general overview, see: R. Huisgen A. Padwa, 1,3-Dipolar Cycloaddition Chemistry 1984 Wiley-Interscience New York 176
28. S.B. Höfling, A.L. Bartuschat, and M.R. Heinrich Angew. Chem., Int. Ed. 49 2010 9769
29. H. Jasch, S. Höfling, and M.R. Heinrich J. Org. Chem. 77 2012 1520
30. S. Fehler, G. Pratsch, and M.R. Heinrich Angew. Chem., Int. Ed. 53 2014 11361
31. 18F-radiochemistry, see: S. Fehler, S. Höfling, A. Bartuschat, S. Maschauer, N. Tschammer, H. Hübner, P. Gmeiner, O. Prante, and M.R. Heinrich Chem. - Eur. J. 20 2014 370
32. O. Tšubrik, K. Kisseljova, and U. Mäeorg Synlett 2006 2391
33. O. Tšubrik, R. Sillard, and U. Mäeorg Synthesis 5 2006 843
34. M. Zhu, and N. Zheng Synthesis 14 2011 2223
35. I.D. Jurberg, and F. Gagosz J. Organomet. Chem. 696 2011 37
36. K. Kisseljova, O. Tšubrik, R. Sillard, S. Mäeorg, and U. Mäeorg Org. Lett. 8 2006 43
37. M. Forchiassin, A. Risaliti, and C. Russo Tetrahedron 37 1981 2921
38. E. Ballaben, M. Forchiassin, P. Nitti, and C. Russo Gazz. Chim. Ital. 123 1993 387
39. I. Sapountzis, and P. Knochel Angew. Chem., Int. Ed. 43 2004 897
40. Cycloaddition of ketenes with N-benzoyldiazenes catalyzed by N-heterocyclic carbenes, see: X.-L. Huang, L. He, P.-L. Shao, and S. Ye Angew. Chem., Int. Ed. 48 2009 192
41. G. Michels, R. Mynott, and M. Regitz Chem. Ber. 121 1988 357
42. T. Kato, and M. Sato J. Org. Chem. 39 1974 3305
43. R.B. Kerber, T.J. Ryan, and S.D. Hsu J. Org. Chem. 39 1974 1215
44. D. Monge, K.D. Jensen, I. Marin, and K.A. Jørgensen Org. Lett. 13 2011 328
45. D. Hong, Y. Zhu, X. Lin, and Y. Wang Tetrahedron 67 2011 650
46. Q.-L. Wang, J.-Y. Fu, L. Peng, Q.-C. Yang, L.-N. Jia, X.-Y. Luo, Y.-Y. Gui, F. Tian, W. Wang, X.-Y. Xu, and L.-X. Wang Tetrahedron Lett. 53 2012 2985
47. For further cycloaddition reactions to azodiesters, see
48. V. Nair, S.M. Mathew, A.T. Biju, and E. Suresh Angew. Chem., Int. Ed. 46 2007 2070
49. L.-T. Shen, L.-H. Sun, and S. Ye J. Am. Chem. Soc. 133 2011 15894
50. The experiments with 2-isocyano-3-phenylpropanoate and 1b were carried out under conditions reported in ref. 18. No triazoles or triazolines could be detected by 1H NMR analysis of the reaction mixtures.
51. The presence of a triazoline was assumed due to a 1H-NMR singlett signal around 5.70 ppm.
52. 2 alone is not sufficient to achieve Boc-cleavage and aromatization.
53. I. Coldham, and R. Hufton Chem. Rev. 105 2005 2765
54. K.V. Kudryavtsev, P.M. Ivantcova, A.V. Churakov, S. Wiedmann, B. Luy, C. Muhle-Goll, N.S. Zefirov, and S. Bräse Angew. Chem., Int. Ed. 52 2013 12736
55. The formation of triazole 8 can be explained by an increased reactivity of the tert-butyl ester on the triazoline stage of the reaction while the decarboxylation of 6p forming product 7 might be favored due to steric reasons.
56. The position of the double bond in triazoline 14 was determined by HSQC and HMBC experiments.
57. For the addition (and cycloaddition) of deprotonated glycine imines to enones, see: Y. Zhang, L. Pan, X. Xu, and Q. Liu RSC Adv. 2 2012 5138
58. For the regioselectivity in cycloadditions of nitrile oxides to Michael systems, see: P. Mayo, T. Hecnar, and W. Tam Tetrahedron 57 2001 5931
59. References for known compounds 3a, d, f, 10 and 13
60. R. Robles-Machín, A. López-Pérez, M. González-Esguevillas, J. Adrio, and J.C. Carretero Chem. Eur. J. 16 2010 9864 Compound 3b
61. T.B. Patrick, M. Shadmehr, A.H. Khan, R.K. Singh, and B. Asmelash J. Fluorine Chem. 143 2012 109 Compounds 3c, h, k
62. J.-P. Mazaleyrat, Y. Goubard, M.-V. Azzini, M. Wakselman, C. Peggion, F. Formaggio, and C. Toniolo Eur. J. Org. Chem. 2002 1232 Compound 3i
63. X. Gu, Z.-J. Xu, V.K.-Y. Lo, and C.-M. Che Synthesis 2012 3307