Synthesis of 5-substituted lH-tetrazoles from nitriles and hydrazoic acid by using a safe and scalable high-temperature microreactor approach

Angewandte Chemie - International Edition

Volumn 49, Issue 39, 2010, Pages 7101-7105

  Gutmann, Bernhard ^a   Roduit, Jean Paul ^b   Kappe, C Oliver ^a   Roberge, Dominique ^b  

^a UNIVERSITY OF GRAZ   (Austria)

^b LONZA AG   (Switzerland)

Author keywords

Cycloaddition; Hydrazoic acid; Microreactors; Process intensification; Tetrazoles

Indexed keywords

CONTINUOUS FLOWS; HIGH TEMPERATURE; HYDRAZOIC ACID; MICRO-REACTOR; MICROREACTORS; PROCESS INTENSIFICATION; RESIDENCE TIME; TETRAZOLES;

CHEMICAL REACTORS; CYANIDES; ORGANIC POLYMERS;

ACIDS;

1H TETRAZOLE; 1H-TETRAZOLE; AZIDE; HYDROGEN AZIDE; NITRILE; TETRAZOLE DERIVATIVE;

ARTICLE; CHEMISTRY; ELECTRONICS; HEAT; INSTRUMENTATION; METHODOLOGY; MICROFLUIDIC ANALYSIS; SYNTHESIS;

AZIDES; HOT TEMPERATURE; MICROFLUIDIC ANALYTICAL TECHNIQUES; MINIATURIZATION; NITRILES; TETRAZOLES;

EID: 77956895241     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201003733     Document Type: Article

References (73)

1. a) R. J. Herr, Bioorg. Med. Chem. 2002, 10, 3379.
2. b) L. V. Myznikov, A. Hrabalek, G. I. Koldobskii, Chem. Heterocycl. Compd. 2007, 43, 1.
3. a) S. J. Wittenberger, Org. Prep. Proced. Int. 1994, 26, 499.
4. b) R. N. Butler in Comprehensive Heterocyclic Chemistry II, Vol. 4 (Eds. : A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon, Oxford, 1996, p. 621.
5. c) P. N. Gaponik, S. V. Voite-khovich, O. A. Ivashkevich, Russ. Chem. Rev. 2006, 75, 507.
6. a) W. G. Finnegan, R. A. Henry, R. Lofquist, J. Am. Chem. Soc. 1958, 80, 3908.
7. b) E. Lieber, T. Enkoji, J. Org. Chem. 1961, 26, 4472.
8. c) P. R. Bernstein, E. P. Vacek, Synthesis 1987, 1133.
9. d) K. Koguro, T. Oga, S. Mitsui, R. Orita, Synthesis 1998, 910.
10. e) B. S. Jursic, B. W. LeBlanc, J. Heterocycl. Chem. 1998, 35, 405.
11. a) M. Alterman, A. Hallberg, J. Org. Chem. 2000, 65, 7984.
12. b) J. -J. Shie, J. -M. Fang, J. Org. Chem. 2007, 72, 3141.
13. c) J. Roh, T. V. Artamonova, K. Vavrova, G. I. Koldobskii, A. Hrabálek, Synthesis 2009, 2175.
14. d) B. Schmidt, D. Meid, D. Kieser, Tetrahedron 2007, 63, 492.
15. a) R. M. Herbst, K. R. Wilson, J. Org. Chem. 1957, 22, 1142.
16. b) J. S. Mihina, R. M. Herbst, J. Org. Chem. 1950, 15, 1082.
17. a) A. Kumar, R. Narayanan, H. Shechter, J. Org. Chem. 1996, 61, 4462.
18. b) G. Venkateshwarlu, A. Premalatha, K. C. Rajanna, P. K. Saiprakash, Synth. Commun. 2009, 39, 4479.
19. c) G. Venkateshwarlu, K. C. Rajanna, P. K. Saiprakash, Synth. Commun. 2009, 39, 426.
20. a) M. Lakshmi Kantam, K. B. S. Kumar, K. P. Raja, J. Mol. Catal. A 2006, 247, 186.
21. b) M. L. Kantam, V. Balasubrahmanyam, K. B. S. Kumar, Synth. Commun. 2006, 36, 1809.
22. c) M. Nasrol-lahzadeh, Y. Bayat, D. Habibi, S. Moshaee, Tetrahedron Lett. 2009, 50, 4435.
23. d) J. He, B. Li, F. Chen, Z. Xu, G. Yin, J. Mol. Catal. A 2009, 304, 135.
24. e) B. Das, C. R. Reddy, D. N. Kumar, M. Krishnaiah, R. Narender, Synlett 2010, 391.
25. a) M. Lakshmi Kantam, K. B. S. Kumar, C. Sridhar, Adv. Synth. Catal. 2005, 347, 1212.
26. b) L. Lang, B. Li, W. Liu, L. Jiang, Z. Xu, G. Yin, Chem. Commun. 2010, 46, 448.
27. Z. P. Demko, K. B. Sharpless, J. Org. Chem. 2001, 66, 7945.
28. a) F. Himo, Z. P. Demko, L. Noodleman, K. B. Sharpless, J. Am. Chem. Soc. 2003, 125, 9983.
29. b) J. -J. Shie, J. -M. Fang, J. Org. Chem. 2003, 68, 1158.
30. c) L. V. Myznikov, J. Roh, T. V. Artamonava, A. Hrabalek, G. I. Koldobskii, Russ. J. Org. Chem. 2007, 43, 765.
31. d) Y. Zhu, Y. Ren, C. Cai, Helv. Chim. Acta 2009, 92, 171.
32. a) B. E. Huff, M. A. Staszak, Tetrahedron Lett. 1993, 34, 8011.
33. b) S. J. Wittenberger, B. G. Donner, J. Org. Chem. 1993, 58, 4139.
34. c) D. Amantini, R. Belaggia, F. Fringuelli, F. Pizzo, L. Vaccaro, J. Org. Chem. 2004, 69, 2896.
35. d) I. V. Bliznets, A. A. Vasil'ev, S. V. Shorshnev, A. E. Stepanov, S. M. Lukyanov, Tetrahedron Lett. 2004, 45, 2571.
36. e) T. Jin, F. Kitahara, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 2008, 49, 2824.
37. f) J. Bonnamour, C. Bolm, Chem. Eur. J. 2009, 15, 4543.
38. a) J. S. McMurray, O. Khabashesku, J. S. Britwistle, W. Wang, Tetrahedron Lett. 2000, 41, 6555.
39. b) Y. Rival, C. G. Wermuth, Synth. Commun. 2000, 30, 1587.
40. c) J. V. Duncia, M. E. Pierce, J. B. Santella, J. Org. Chem. 1991, 56, 2395.
41. d) D. P. Curran, S. Hadida, S. -Y. Kim, Tetrahedron 1999, 55, 8997.
42. a) C. Arnold, D. N. Thatcher, J. Org. Chem. 1969, 34, 1141.
43. b) V. Aureggi, G. Sedelmeier, Angew. Chem. 2007, 119, 8592
44. Angew. Chem. Int. Ed. 2007, 46, 8440.
45. F. Himo, Z. P. Demko, L. Noodleman, K. B. Sharpless, J. Am. Chem. Soc. 2002, 124, 12210.
46. J. von Braun, W. Keller, Ber. Dtsch. Chem. Ges. 1932, 65, 1677.
47. a) M. E. Kopach, M. M. Murray, T. M. Braden, M. E. Kobierski, O. L. Williams, Org. Process Res. Dev. 2009, 13, 152, and references therein; for further safety and general chemical properties of HN3
48. b) Encyclopedia of Inorganic Chemistry, 2nd ed. (Ed. : R. B. King), Wiley-VCH, Weinheim, 2005.
49. c) J. -P. Hagenbuch, Chimia 2003, 57, 773.
50. a) K. Geyer, T. Gustafson, P. H. Seeberger, Synlett 2009, 2382.
51. b) R. L. Hartman, K. F. Jensen, Lab Chip 2009, 9, 2495.
52. c) C. Wiles, P. Watts, Eur. J. Org. Chem. 2008, 1655.
53. Microreactors in Organic Synthesis and Catalysis (Ed. : T. Wirth), Wiley-VCH, Weinheim, 2008.
54. )Handbook of Micro Reactors (Eds. : V. Hessel, J. C. Schouten, A. Renken, Y. Wang, J. -I. Yoshida), Wiley-VCH, Weinheim, 2009.
55. c) J. -I. Yoshida, Flash Chemistry-Fast Organic Synthesis in Microsystems, Wiley-VCH, Weinheim, 2008.
56. T. Razzaq, C. O. Kappe, Chem. Asian J. 2010, 5, 1274.
57. a) D. M. Roberge, M. Gottsponer, M. Eyholzer, N. Kockmann, Chem. Today 2009, 27, 8.
58. b) D. M. Roberge, B. Zimmermann, F. Rainone, M. Gottsponer, M. Eyholzer, N. Kockmann, Org. Process Res. Dev. 2008, 12, 905.
59. c) V. Hessel, S. Hardt, H. Löwe, Micro Chemical Process Engineering, Wiley-VCH, Weinheim, 2004.
60. a) H. R. Sahoo, J. G. Kralj, K. F. Jensen, Angew. Chem. 2007, 119, 5806
61. Angew. Chem. Int. Ed. 2007, 46, 5704.
62. b) A. R. Bogdan, N. W. Sach, Adv. Synth. Catal. 2009, 351, 849.
63. c) J. C. Brandt, T. Wirth, Beilstein J. Org. Chem. 2009, 5, 30.
64. d) see also Ref. [16a].
65. M. Treu, T. Karner, R. Kousek, H. Berger, M. Mayer, D. B. McConnell, A. Stadler, J. Comb. Chem. 2008, 10, 863.
66. a) M. Damm, C. O. Kappe, Mol. Diversity 2009, 13, 529.
67. b) D. Obermayer, B. Gutmann, C. O. Kappe, Angew. Chem. 2009, 121, 8471
68. Angew. Chem. Int. Ed. 2009, 48, 8321.
69. A more detailed description of reaction optimization is presented in the Supporting Information.
70. For further details on the FlowSyn reactor and experimental setup see the Supporting Information and www.uniqsis.com.
71. Sulfinert is a Siltek-treated stainless-steel coil (i. e. chemical vapor deposited multilayer silica coating) that has the advan-tages of Teflon coatings or glass/fused silica coils without the problems with gas permeability and temperature limitations associated with polymeric coatings such as Teflon coatings, and with far higher flexibility and durability than glass/fused silica coils. The temperature limit of these coils is 600 °C. For further information, see: www.restek.com.
72. On an industrial scale, this chemical quench step (HN3 + HNO2→N2O + N2 + H2O, Ref. [16b]) could be performed inline in flow as the reaction mixture remains homogeneous upon addition of aqueous NaNO2.
73. M. W. Bedore, N. Zaborenko, K. F. Jensen, T. F. Jamison, Org. Process Res. Dev. 20l0, 14, 432.