Lewis acid mediated tandem reaction of propargylic alcohols to tetrazoles involving C-O- and C-C-bond cleavage reactions and a C-N-bond formation

Chemistry - A European Journal

Volumn 20, Issue 38, 2014, Pages 12046-12050

  Song, Xian Rong ^a   Han, Ya Ping ^a   Qiu, Yi Feng ^a   Qiu, Zi Hang ^a   Liu, Xue Yuan ^a   Xu, Peng Fei ^a   Liang, Yong Min ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

1 aryl 5 arylvinyl tetrazoles; C C bond cleavage; C N bond formation; Lewis acids; propargylic alcohols

Indexed keywords

ALCOHOLS; FUNCTIONAL GROUPS; SYNTHESIS (CHEMICAL);

1-ARYL-5-ARYLVINYL-TETRAZOLES; C-C BOND CLEAVAGES; C-N BOND FORMATIONS; LEWIS ACID; PROPARGYLIC ALCOHOLS;

COVALENT BONDS;

EID: 84912559793     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201403752     Document Type: Article

References (68)

1. D. R. Armour, K. M. L. Chung, M. Congreve, B. Evans, S. Guntrip, T. Hubbard, C. Kay, D. Middlemiss, J. E. Mordaunt, N. A. Pegg, M. V. Vinader, P. Ward, S. P. Watson, Bioorg. Med. Chem. Lett. 1996, 6, 1015
2. D. Moderhack, J. Prakt. Chem./Chem.-Ztg. 1998, 340, 687
3. D. Potts, P. J. Stevenson, N. Thompson, Tetrahedron Lett. 2000, 41, 275
4. A. Fettes, E. M. Carreira, Angew. Chem. 2002, 114, 4272
5. Angew. Chem. Int. Ed. 2002, 41, 4098
6. P. Jankowski, K. Plesniak, J. Wicha, Org. Lett. 2003, 5, 2789
7. D. Enders, A. Lenzen, M. Muller, Synthesis 2004, 1486
8. L. M. T. Frija, I. V. Khmelinskii, M. L. S. Cristiano, Tetrahedron Lett. 2005, 46, 6757
9. J. Quintin, G. Lewin, J. Nat. Prod. 2004, 67, 1624
10. M. J. Schnermann, D. L. Boger, J. Am. Chem. Soc. 2005, 127, 15704
11. L. V. Myznikov, A. Hrabalek, G. I. Koldobskii, Chem. Heterocycl. Compd. 2007, 43, 1
12. B. J. Al-Hourani, S. K. Sharma, J. Y. Mane, J. Tuszynski, V. Baracos, T. Kniess, M. Suresh, J. Pietzsch, F. Wuest, Bioorg. Med. Chem. Lett. 2011, 21, 1823.
13. A. L. Tökés, G. Litkei, Synth. Commun. 1993, 23, 895
14. H. Suzuki, Y. S. Hwang, C. Nakaya, Y. Matano, Synthesis 1993, 1218
15. A. S. El-Ahl, S. S. Elmorsy, H. Soliman, F. A. Amer, Tetrahedron Lett. 1995, 36, 7337
16. A. G. Schultz, A. Wang, C. Alva, A. Sebastian, S. D. Glick, D. C. Deecher, J. M. Bidlack, J. Med. Chem. 1996, 39, 1956.
17. R. N. Butler, D. A. O. Donoghue, J. Chem. Res., Synop. 1983, 18.
18. J. Zabrocki, J. B. Dunbar, Jr., K. W. Marshall, M. V. Toth, G. R. Marshall, J. Org. Chem. 1992, 57, 202
19. E. W. Thomas, Synthesis 1993, 767
20. A. LeTiran, J. P. Stables, H. Kohn, Bioorg. Med. Chem. 2001, 9, 2693
21. J. Xiao, X. Zhang, D. Wang, C. Yuan, J. Fluorine Chem. 1999, 99, 83
22. A. F. Hegarty, N. M. Tynan, S. Fergus, J. Chem. Soc. Perkin Trans. 2 2002, 1328.
23. T. V. Artamonova, A. B. Zhivich, M. Yu. Dubinskii, G. I. Koldobskii, Synthesis 1996, 1428.
24. A. R. Katritzky, C. Cai, N. K. Meher, Synthesis 2007, 1204.
25. D. Cantillo, B. Gutmann, C. O. Kappe, J. Am. Chem. Soc. 2011, 133, 4465
26. Angew. Chem. 2011, 123, 3587
27. Angew. Chem. Int. Ed. 2011, 50, 3525
28. F. Couty, F. Durrat, D. Prim, Tetrahedron Lett. 2004, 45, 3725
29. F. Himo, Z. P. Demko, L. Noodleman, K. B. Sharpless, J. Am. Chem. Soc. 2003, 125, 9983
30. Z. P. Demko, K. B. Sharpless, Angew. Chem. 2002, 114, 2217
31. Angew. Chem. Int. Ed. 2002, 41, 2113.
32. F. Chen, C. Qin, Y. Cui, N. Jiao, Angew. Chem. 2011, 123, 11689
33. Angew. Chem. Int. Ed. 2011, 50, 11487
34. B. V. Rokade, K. Gadde, K. R. Prabhu, Adv. Synth. Catal. 2014, 356, 946.
35. M. Gaydou, A. M. Echavarren, Angew. Chem. 2013, 125, 13710
36. Angew. Chem. Int. Ed. 2013, 52, 13468.
37. X. Zhang, W. T. Teo, Sally, P. W. H. Chan, J. Org. Chem. 2010, 75, 6290
38. X. Zhang, W. T. Teo, P. W. H. Chan, Org. Lett. 2009, 11, 4990
39. W. Huang, Q. Shen, J. Wang, X. Zhou, J. Org. Chem. 2008, 73, 1586
40. K. Lee, P. H. Lee, Org. Lett. 2008, 10, 2441
41. R. Sanz, D. Miguel, A. Martinez, J. M. Alvarez-Gutierrez, F. Rodriguez, Org. Lett. 2007, 9, 727.
42. K.-G. Ji, J. Chen, H.-T. Zhu, F. Yang, A. Shaukat, Y.-M. Liang, Chem. Eur. J. 2011, 17, 305
43. K.-G. Ji, H.-T. Zhu, F. Yang, A. Shaukat, Xiao-F. Xia, Y.-F. Yang, X.-Y. Liu, Y.-M. Liang, J. Org. Chem. 2010, 75, 5670
44. K.-G. Ji, X.-Z. Shu, S.-C. Zhao, H.-T. Zhu, Y.-N. Niu, X.-Y. Liu, Y.-M. Liang, Org. Lett. 2009, 11, 3206.
45. H. Zhang, H. Tanimoto, T. Morimoto, Y. Nishiyama, K. Kakiuchi, Org. Lett. 2013, 15, 5222.
46. G. Busca, Chem. Rev. 2007, 107, 5366.
47. CCDC 993234 (2a) contains the supplementary crystallographic data for this paper (see the Supporting Information). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif
48. 1-Methyl-1-phenyl-substituted tertiary propargylic alcohol 1y tends to undergo an intramolecular dehydration under the standard conditions to afford the 1,3-enyne compound 5y, see:, S. Swaminathan, K. V. Narayanan, Chem. Rev. 1971, 71, 429.
49. V. Cadierno, S. E. Garca-Garrido, J. Gimeno, Adv. Synth. Catal. 2006, 348, 101
50. D. A. Engel, G. B. Dudley, Org. Lett. 2006, 8, 4027
51. M. Stefanoni, M. Luparia, A. Porta, G. Zanoni, G. Vidari, Chem. Eur. J. 2009, 15, 3940
52. D. A. Engel, G. B. Dudley, Org. Biomol. Chem. 2009, 7, 4149
53. V. Cadierno, P. Crochet, S. E. Gaca-Garrido, J. Gimino, Dalton Trans. 2010, 39, 4015
54. B. M. Trost, X. Luan, Y. Miller, J. Am. Chem. Soc. 2011, 133, 12824
55. M. N. Pennell, M. G. Unthank, P. Turner, T. D. Sheppard, J. Org. Chem. 2011, 76, 1479
56. D. Wang, Y. Zhang, A. Harris, L. N. S. Gautam, Y. Chen, X. Shi, Adv. Synth. Catal. 2011, 353, 2584.
57. K. F. Schmidt, Z. Angew. Chem. 1923, 35, 511
58. H. Wolff, Org. React. 1946, 3, 307
59. G. R. Krow, Tetrahedron 1981, 37, 1283
60. J. Aube, G. L. Milligan, J. Am. Chem. Soc. 1991, 113, 8965
61. S. Bräse, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem. 2005, 117, 5320
62. Angew. Chem. Int. Ed. 2005, 44, 5188
63. S. Lang, J. A. Murphy, Chem. Soc. Rev. 2006, 35, 146
64. S. Grecian, J. Aubé, in Organic Azides: Syntheses and Applications (Eds.:, S. Bräse, K. Banert,), Wiley, Chichester 2010, p. 191
65. A. Wrobleski, T. C. Coombs, C. W. Huh, S.-W. Li, J. Aubé, Org. React. 2012, 78, 1.
66. M. I. K. Amer, B. L. Booth, J. Chem. Res., Synop. 1993, 4
67. E. Cubero, M. Orozco, F. J. Luque, J. Am. Chem. Soc. 1998, 120, 4723
68. T. Lioux, G. Gosselin, C. Mathé, Eur. J. Org. Chem. 2003, 3997.