Protected diazonium salts: a continuous-flow preparation of triazenes including the anticancer compounds dacarbazine and mitozolomide

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Schotten, Christiane; Aldmairi, Abdul Hadi; Sagatov, Yerbol; Shepherd, Martyn; Browne, Duncan L.;
(2016)

Herein, we report a continuous-flow process for the preparation of triazenes, whereby diazonium salts are generated and converted into their masked or protected triazene derivatives. Key to realizing the process, which is applicable to a wide range of substrates, is the... View more
  • References (24)
    24 references, page 1 of 3

    1. (a) Mo, F.; Dong, G.; Zhang, Y.; Wang, J. Org. Biomol. Chem. 2013, 11, AQ11 1582; (b) Kölmel, D. K.; Jung, N.; Bräse, S. Aust. J. Chem. 2014, 67, 328; (c) Roglans, A.; Pla-Quintana, A.; Moreno-Mañas, M. Chem. Rev. 2006, 106, 4622; (d) Felpin, F.-X.; Nassar-Hardy, L.; Le Callonnec, F.; Fouquet, E. Tetrahedron 2011, 67, 2815; (e) Taylor, J. G.; Moro, A. V.; Correia, C. R. D. Eur. J. Org. Chem. 2011, 1403.

    2. (a) Mich, T. F.; Nienhouse, E. J.; Farina, T. E.; Tufariello, J. J. J. Chem. Ed. 1968, 45, 272; (b) Sheng, M.; Frurip, D.; Gorman, D. J. Loss Prevent. Proc. 2015, 38, 114.

    3. For reviews on continuous-flow processing of diazonium salts and diazo compounds, see: (a) Deadman, B. J.; Collins, S. G.; Maguire, A. R. Chem. Eur. J. 2015, 21, 2298; (b) Müller, S. T. R.; Smith, D.; Hellier, P.; Wirth, T. Synlett 2014, 25, 871; (c) Oger, N.; Le Grognec, E.; Felpin, F.-X. Org. Chem. Front. 2015, 2, 590-614.

    5. (a) Lazny, R.; Sienkiewicz, M.; Bräse, S. Tetrahedron 2001, 57, 5825- 5832; (b) Kimball, D. B.; Haley, M. M. Angew. Chem., Int. Ed. 2002, 41, 3338- 3351; (c) May, C.; Moody, C. J. J. Chem. Soc. 1988, 2, 247-250; (d) Vaughan, K. Org. Prep. Proc. Int. 2001, 33, 59-74.

    6. (a) Liu, C.-Y.; Knochel, P. J. Org. Chem. 2007, 72, 7106-7115; (b) Goeminne, A.; Scammells, P. J.; Devine, S. M.; Flynn, B. L. Tetrahedron Lett. 2010, 51, 6882-6885; (c) Saeki, T.; Matsunaga, T.; Son, E.-C.; Tamao, K. Adv. Synth. Catal. 2004, 346, 1689-1692; (d) Saeki, T.; Son, E.-C.; Tamao, K. Org. Let. 2004, 6, 617- 619; (e) Bräse, S.; Schroen, M. Angew. Chem., Int. Ed. 1999, 38, 1071-1073; (f) Barbero, M.; Degani, I.; Diulgheroff, N.; Dughera, S.; Fochi, R. Synthesis 2001, 14, 2180-2190; (g) Döbele, M.; Vanderheiden, S.; Jung, N.; Bräse, S. Angew. Chem., Int. Ed. 2010, 49, 5986-5988; (h) Wang, C.; Chen, H.; Wang, Zh.; Chen, J.; Huang, Y. Angew. Chem., Int. Ed. 2012, 51, 7242-7245; (i) Sun, H.; Wang, C.; Yang, Y.-F.; Chen, P.; Wu, Y.-D.; Zhang, X. J. Org. Chem. 2014, 79, 11863-11872; (j) Lazny, R.; Poplawski, J.; Kobberling, J.; Enders, D.; Bräse, S. Synlett 1999, 8, 1304-1306; (k) Liu, C.-Y.; Knochel, P. Org. Let. 2005, 7, 2543-2546; (l) Lormann, M.; Dahmen, S.; Bräse, S. Tetrahedron Lett. 2000, 41, 3813-3816; (m) Satyamurthy, N.; Barrio, J. R.; Bida, G. T.; Phelps, M. E. Tetrahedron Lett. 1990, 31, 4409-4412; (n) Hudson, J. L.; Jian, H.; Leonard, A. D.; Stephenson, J. J.; Tour, J. M. Chem. Mater. 2006, 18, 2766-2770; (o) Gross, M. L.; Blank, D. H.; Welch, W. M. J. Org. Chem. 1993, 58, 2104-2109; (p) Patrick, T. B.; Juehne, T.; Reeb, E.; Hennessy, D. Tetrahedron Lett. 2001, 42, 3553-3354.

    7. (a) Reisman, S. E.; Ready, J. M.; Weiss, M. M.; Hasuoka, A.; Hirata, M.; Tamaki, K.; Smith, C. J.; Wood, J. L. J. Am. Chem. Soc. 2008, 130, 2087-2100; (b) Hafner, A.; Bräse, S. Angew. Chem., Int. Ed. 2012, 51, 3713-3715; (c) Wang, C.; Chen, H.; Wang, Zh.; Chen, J.; Huang, Y. Angew. Chem., Int. Ed. 2012, 51, 7242-7245; (d) Hafner, A.; Feuerstein, T. J.; Bräse, S. Org. Let. 2013, 15, 3468- 3471; (e) Hafner, A.; Bihlmeier, A.; Nieger, M.; Klopper, W.; Bräse, S. J. Org. Chem. 2013, 78, 7938-7948.

    8. (a) Zhang, F.; Spring, D. R. Chem. Soc. Rev. 2014, 43, 6906-6919; (b) Wang, C.; Huang, Y. Synlett 2013, 24, 145-149.

    9. For some reviews on hazardous flow, see: (a) Gutmann, B.; Cantillo, D.; Kappe, C. O. Angew. Chem., Int. Ed. 2015, 54, 6688-6728; (b) Kulkarni, A. A. Beilstein J. Org. Chem. 2014, 10, 405-424; (c) Yoshida, J.-I.; Takahashi, Y.; Nagaki, A. Chem. Commun. 2013, 49, 9896; (d) Gutmann, B.; Kappe, C. O. Chim. Oggi Chem. Today 2015, 33, 3.

    10. (a) Hartwig, J.; Ceylan, S.; Kupracz, L.; Coutable, L.; Kirschning, A. Angew. Chem., Int. Ed. 2013, 52, 9813; (b) Ghislieri, D.; Gilmore, K.; Seeberger, P. H. Angew. Chem., Int. Ed. 2015, 54, 678; (c) Newton, S.; Carter, C. F.; Pearson, C. M.; Alves, L. de C.; Lange, H.; Thansandote, P.; Ley, S. V. Angew. Chem., Int. Ed. 2014, 53, 4915; (d) Kupracz, L.; A. Kirschning Adv. Synth. Catal. 2013, 355, 3375; (e) Pastre, J. C.; Browne, D. L.; O'Brien, M.; Ley, S. V. Org. Process Res. Dev. 2013, 17, 1183; (f) Murray, P. R. D.; Browne, D. L.; Pastre, J. C.; Butters, C.; Guthri, D.; Ley, S. V. Org. Process Res. Dev. 2013, 17, 1192; (g) Battilocchio, C.; Baxendale, I. R.; Biava, M.; Kitching, M. O.; Ley, S. V. Org. Process Res. Dev. 2012, 16, 798; (h) Kabeshov, M. A.; Musio, B.; Murray, P. R. D.; Browne, D. L.; Ley, S. V. Org. Lett. 2014, 16, 4618; (i) Lau, S.-H.; Galván, A.; Merchant, R. R.; Battilocchio, C.; Souto, J. A.; Berry, M. B.; Ley, S. V. Org. Lett. 2015, 17, 3218; (j) Correia, C. A.; Gilmore, K.; McQuade, D. T.; Seeberger, P. H. Angew. Chem., Int. Ed. 2015, 54, 4945; (k) Tsubogo, T.; Oyamada, H.; Kobayash, S. Nature 2015, 520, 329; (l) Adamo, A.; Beingessner, R. L.; Behnam, M.; Chen, J.; Jamison, T. F.; Jensen, K. F.; Monbaliu, J.-C. M.; Myerson, A. S.; Revalor, E. M.; Snead, D. R.; Stelzer, T.; Weeranoppanant, N.; Wong, S. Y.; Zhang, P. Science 2016, 352, 61-67.

    11. For handling solids in flow, see: (a) Deadman, B. J.; Browne, D. L.; Baxendale, I. R.; Ley, S. V. Chem. Eng. Technol. 2015, 38, 259-264; (b) Browne, D. L.; Deadman, B. J.; Ashe, R.; Baxendale, I. R.; Ley, S. V. Org. Proc. Res. Dev. 2011, 15, 693-697; (c) Hartman, R. L. Org. Process Res. Dev. 2012, 16, 870- 887; (d) Sedelmeier, J.; Ley, S. V.; Baxendale, I. R.; Baumann, M. Org. Lett. 2010, 12, 3618-3621; (e) Kelly, C. B.; Lee, C. X.; Leadbeater, N. E. Tetrahedron Lett. 2011, 52, 263-265; (f) Noel, T.; Naber, J. R.; Hartman, R. L.; McMullen, J. P.; Jensen, K. F.; Buchwald, S. L. Chem. Sci. 2011, 2, 287-290.

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