DOI QR코드

DOI QR Code

Reaction of Tosylmethyl Isocyanide with N-Heteroaryl Formamidines: an Alternative Approach to the Synthesis of N-Heteroaryl Tosylimidazoles

  • Received : 2013.04.11
  • Accepted : 2013.06.07
  • Published : 2013.09.20

Abstract

Keywords

References

  1. Elliot, G. I.; Konopelski, J. P. Org. Lett. 2000, 2, 3055. https://doi.org/10.1021/ol006271w
  2. Boehm, J. C.; Bower, M. J.; Gallagher, T. F.; Kassis, Sh.; Johnson, S. R.; Adams, J. L. Bioorg. & Med. Chem. Lett. 2001, 11, 1123. https://doi.org/10.1016/S0960-894X(01)00163-9
  3. Gallagher, T. F.; Boehm, J. Ch.; Adams, J. L. US Pat. 6335340, B1, 2002.
  4. Cozzi, P.; Carganico, G.; Fusar, D.; Grossoni, M.; Menichincheri, M.; Princiroli, V.; Tonani, R.; Vaghi, F.; Salvati, P. J. Med. Chem. 1993, 36, 2964. https://doi.org/10.1021/jm00072a017
  5. Trejo, A.; Arzeno, H.; Browner, M.; Chanda, S.; Cheng, S.; Comer, D. J. Med. Chem. 2003, 19, 4702.
  6. Gungor, T.; Fouquet, A.; Teulon, J.-M.; Provost, D.; Cazes, M.; Cloarec, A. J. Med. Chem. 1992, 35, 4455. https://doi.org/10.1021/jm00101a024
  7. Lo, Y. S.; Nolan, J. C.; Maren, T. H.; Welstead, W. J., Jr.; Gripshover, D. F.; Shamblee, D. A. J. Med. Chem. 1992, 35, 4790. https://doi.org/10.1021/jm00104a003
  8. Antilla, J. C.; Baskin, J. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2004, 69, 5578. https://doi.org/10.1021/jo049658b
  9. Johnson, A. L.; Kauer, J. C.; Sharma, D. C.; Dorfman, R. I. J. Med. Chem. 1969, 12, 1024. https://doi.org/10.1021/jm00306a013
  10. Gorvin, J. H. J. Chem. Soc. Perkin Trans. 1 1988, 1331.
  11. Thomas, A. W.; Ley, S. V. Angew. Chem. Int. Ed. 2003, 42, 5400. https://doi.org/10.1002/anie.200300594
  12. Antilla, J. C.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 11684. https://doi.org/10.1021/ja027433h
  13. Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. https://doi.org/10.1021/ja016226z
  14. Cristau, H. J.; Cellier, P. P.; Spindler, J. F.; Taillefer, M. Eur. J. Org. Chem. 2004, 695.
  15. Cristau, H. J.; Cellier, P. P.; Splinder, J. F.; Taillefer, M. Chem. Eur. J. 2004, 10, 5607. https://doi.org/10.1002/chem.200400582
  16. Van Leusen, A. M.; Oldenziel, O. H. Tetrahedron Lett. 1972, 23, 2373.
  17. Van Leusen, D.; Van Leusen A. M. In Organic Reactions; Overman, L. E., Ed.; Wiley & Sons Inc.: 2001; Vol. 57, Chap. 3, pp 417-477.
  18. Taylor, E. C.; LaMattina, J. M.; Tseng, C.-P. J. Org, Chem. 1982, 47, 2043. https://doi.org/10.1021/jo00132a013
  19. Cunningham, I. D.; Bladen, J. S.; Llor, J.; Munoz, L.; Sharratt, A. P. J. Chem. Soc. Perkin Trans. 2 1991, 1747.
  20. Dell'Erba. C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1997, 53, 2125. https://doi.org/10.1016/S0040-4020(96)01108-8
  21. Katritzky, A. R.; Cheng, D.; Musgrave, R. P. Heterocycles 1997, 44, 67. https://doi.org/10.3987/COM-95-S5
  22. Ireland, S. M.; Tye, H.; Whittaker, M. Tetrahedron Lett. 2003, 44, 4369. https://doi.org/10.1016/S0040-4039(03)00941-9
  23. Katagiri, N.; Niwa, R.; Kato, T. Chem. Pharm. Bull. 1983, 31, 2899. https://doi.org/10.1248/cpb.31.2899
  24. Cotton, F. A.; Lei, P.; Murillo, C. A.; Wang, L.-Sh. Inorg. Chim. Acta 2003, 349, 165. https://doi.org/10.1016/S0020-1693(03)00092-6
  25. Cherng, Y.-J. Tetrahedron 2002, 58, 887. https://doi.org/10.1016/S0040-4020(01)01182-6

Cited by

  1. ChemInform Abstract: Reaction of Tosylmethyl Isocyanide with N-Heteroaryl Formamidines: An Alternative Approach to the Synthesis of N-Heteroaryl Tosylimidazoles. vol.45, pp.7, 2014, https://doi.org/10.1002/chin.201407180
  2. Aryl Azides as Forgotten Electrophiles in the Van Leusen Reaction: A Multicomponent Transformation Affording 4-Tosyl-1-arylimidazoles vol.84, pp.24, 2013, https://doi.org/10.1021/acs.joc.9b02546