DOI QR코드

DOI QR Code

Metal Free Quick Introduction of Azole in to Azine Nucleus: Acid Catalyzed Reissert-Henze Reaction

  • Velavan, A. (Nycomed Pharma- a Takeda company) ;
  • Mondal, Dibyendu (Nycomed Pharma- a Takeda company) ;
  • Survase, Sachin (Nycomed Pharma- a Takeda company)
  • Received : 2013.06.13
  • Accepted : 2013.08.01
  • Published : 2013.11.20

Abstract

Keywords

References

  1. Shreder, K. R.; Cajica, J.; Du, L.; Fraser, A.; Hu, Y.; Kohno, Y.; Lin, E. C. K.; Liu, S. J.; Okerberg, E.; Pham, Lan; Wu, J.; Kozarich, J. W. Bioorg. Med. Chem. Lett. 2009, 19, 4743. https://doi.org/10.1016/j.bmcl.2009.06.053
  2. Yamada, M.; Yura, T.; Morimoto, M.; Harada, T.; Yamada, K.; Honma, Y.; Kinoshita, M.; Sugiura, M. J. Med. Chem. 1996, 39, 596. https://doi.org/10.1021/jm950610n
  3. Su, D.-S.; Lim, J. J.; Tinney, E.; Wan, B.-L.; Young, M. B.; Anderson, K. D.; Rudd, D.; Munshi, V.; Bahnck, C.; Felock, P. J.; Lu, M.; Lai, M.-T.; Touch, S.; Moyer, G.; Di Stefano, D. J.; Flynn, J. A.; Liang, Y.; Sanchez, R.; Perlow-Poehnelt, R.; Miller, M.; Vacca, J. P.; Williams, T. M.; Anthony, N. J. J. Med. Chem. 2009, 52, 7163. https://doi.org/10.1021/jm901230r
  4. Lu, R.-J.; Tucker, J. A.; Zinevitch, T.; Kirichenko, O.; Konoplev, V.; Kuznetsova, S.; Sviridov, S.; Pickens, J.; Tandel, S.; Brahmachary, E.; Yang, Y.; Wang, J.; Freel, S.; Fisher, S.; Sullivan, A.; Zhou, J.; Stanfield-Oakley, S.; Greenberg, M.; Bolognesi, D.; Bray, B.; Koszalka, B.; Jeffs, P.; Khasanov, A.; Ma, Y.-A.; Jeffries, C.; Liu, C.; Proskurina, T.; Zhu, T.; Chucholowski, A.; Li, R.; Sexton, C. J. Med. Chem. 2007, 50, 6535. https://doi.org/10.1021/jm070650e
  5. Lange, J. H. M.; Van Stuivenberg, H. H.; Coolen, H. K. A. C.; Adolfs, T. J. P.; McCreary, A. C.; Keizer, H. G.; Wals, H. C.; Veerman, W.; Borst, A. J. M.; de Looff, W.; Verveer, P. C.; Kruse, C. G. J. Med. Chem. 2005, 48, 1823. https://doi.org/10.1021/jm040843r
  6. Ohmori, J.; Shimizu-Sasamata, M.; Okada, M.; Sakamoto, S. J. Med. Chem. 1997, 40, 2053. https://doi.org/10.1021/jm960664c
  7. Ohmori, J.; Kubota, H.; Shimizu-Sasamata, M.; Okada, M.; Sakamoto, S. J. Med. Chem. 1996, 39, 1331. https://doi.org/10.1021/jm950304+
  8. 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
  9. Lee, H.-G.; Won, J.-E.; Kim, M.-J.; Park, S.-E.; Jung, K.-J.; Kim, B. R.; Lee, S.-G.; Yoon, Y.-J. J. Org. Chem. 2009, 74, 5675. https://doi.org/10.1021/jo900752z
  10. Suresh, P.; Pitchumani, K. J. Org. Chem. 2008, 73, 9121. https://doi.org/10.1021/jo801811w
  11. Huang, Y.-Z.; Gao, J.; Ma, H.; Miao, H.; Xu, J. Tetrahedron Lett. 2008, 49, 948. https://doi.org/10.1016/j.tetlet.2007.12.026
  12. Ma, H.-C.; Jiang, X.-Z. J. Org. Chem. 2007, 72, 8943. https://doi.org/10.1021/jo7015983
  13. Zhu, L.; Guo, P.; Li, G.; Lan, J.; Xie, R.; You, J. J. Org. Chem. 2007, 72, 8535. https://doi.org/10.1021/jo0712289
  14. Kantam, M. L.; Yadav, J.; Laha, S.; Sreedhar, B.; Jha, S. Adv. Synth. Catal. 2007, 349, 1938. https://doi.org/10.1002/adsc.200600483
  15. Katritzky, A. R.; Lagowski, J. M. Chemistry of the Heterocyclic N-Oxides; Academic Press: London, 1971; p 300.
  16. Abramovitch, R. A.; Smith, E. M. Chem. Heterocycl. Compd. 1974, 14, 114.
  17. Katritzky, A. R.; Kurz, T.; Zhang, S.; Voronkov, M. Heterocycles 2001, 55, 1703. https://doi.org/10.3987/COM-01-9256
  18. Storz, T.; Bartberger, M. D.; Sukits, S.; Wilde, C.; Soukup, T. Synthesis 2008, 2, 201.
  19. Lominac, W. J.; D'Angelo, M. L.; Smith, M. D.; Ollison, D. A.; Hanna, J. M., Jr. Tetrahedron Lett. 2012, 53, 906. https://doi.org/10.1016/j.tetlet.2011.12.055
  20. Shoji, T.; Okada, K.; Ito, S.; Toyota, K.; Morita, N. Tetrahedron Lett. 2010, 51, 5127. https://doi.org/10.1016/j.tetlet.2010.07.090
  21. Klemm, L. H.; Muchiri, D. R. J. Heterocycl. Chem. 1983, 20, 213.
  22. Nishiwaki, N.; Minakata, S.; Komatsu, M.; Yoshiki Ohshiro, Y. Chem. Lett. 1989, 773.
  23. Farrell, R. P.; Elipe, M. V. S.; Bartberger, M. D.; Tedrow, J. S.; Vounatsos, F. Org. Lett. 2013, 15, 168. https://doi.org/10.1021/ol303218p
  24. Manley, P. J.; Bilodeau, M. T. Org. Lett. 2002, 4, 3127. https://doi.org/10.1021/ol0264556
  25. Couturier, M.; Caron, L.; Tumidajski, S.; Jones, K.; White, T. D. Org. Lett. 2006, 8, 1929. https://doi.org/10.1021/ol060473w
  26. Keith, J. M. J. Org. Chem. 2008, 73, 327. https://doi.org/10.1021/jo702038g
  27. Keith, J. M. J. Org. Chem. 2010, 75, 2722. https://doi.org/10.1021/jo1001017
  28. Kurvatov, Y. V.; Solekhova, M. A. Russ. J. Org. Chem. 2007, 43, 1696. https://doi.org/10.1134/S1070428007110176
  29. Yin, J.; Xiang, B.; Huffman, M. A.; Raab, C. E.; Davies, I. W. J. Org. Chem. 2007, 72, 4554. https://doi.org/10.1021/jo070189y
  30. Woodman, E. K.; Chaffey, J. G. K.; Philip, A.; Hopes, P. A.; Hose, D. R. J.; Gilday, J. P. Org. Process Res. Dev. 2009, 13, 106. https://doi.org/10.1021/op800226b
  31. Velavan, A.; Sumathi, S.; Balasubramanian, K. K. Org. Biomol. Chem. 2012, 10, 6420. https://doi.org/10.1039/c2ob25412c
  32. Heller, S. T.; Fu, T.; Sarpong, R. Org. Lett. 2012, 14, 1970. https://doi.org/10.1021/ol300339q
  33. Pal, R.; Sarkar, T.; Khasnobis, S. ARKIVOC 2012, 570-609.

Cited by

  1. Functionalization of a Pyridine Framework through Intramolecular Reissert–Henze Reaction of N‐(Carbamoyloxy)pyridinium Salts and Unexpected Insertion of Ethereal Solvents vol.2015, pp.18, 2013, https://doi.org/10.1002/ejoc.201500443