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A Convenient One-Pot Method for the Synthesis of N-Methoxy-N-methyl Amides from Carboxylic Acids

  • Kim, Joong-Gon (Biotechnology Division, Hanwha Chemical Research and Development Center) ;
  • Jang, Doo-Ok (Department of Chemistry, Yonsei University)
  • Published : 2010.01.20

Abstract

Keywords

References

  1. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815. https://doi.org/10.1016/S0040-4039(01)91316-4
  2. Balasubramaniam, S.; Aidhen, I. S. Synthesis 2008, 23, 3707.
  3. Banwell, M.; Edwards, A.; Smith, J.; Hame, E.; Verdier-Pinard, P. J. Chem. Soc., Perkin Trans 1 2000, 1497.
  4. Perez, M.; del Pozo, C.; Reyes, F.; Rodriguez, A.; Francesch, A.; Echavarren, A. M.; Cuevas, C. Angew. Chem., Int. Ed. 2004, 43, 1724. https://doi.org/10.1002/anie.200353313
  5. Mulzer, J.; Berger, M. J. Org. Chem. 2004, 69, 891. https://doi.org/10.1021/jo035391p
  6. Zanatta, S. D.; White, J. M.; Rizzacasa, M. A. Org. Lett. 2004, 6, 1041. https://doi.org/10.1021/ol049873e
  7. Davis, F. A.; Prasad, K. R.; Nolt, M. B.; Wu, Y. Z. Org. Lett. 2003, 5, 925. https://doi.org/10.1021/ol034119z
  8. Evans, D. A.; Connell, B. T. J. Am. Chem. Soc. 2003, 125, 10899. https://doi.org/10.1021/ja027638q
  9. Vanderwal, C. D.; Vosburg, D. A.; Weiler, S.; Sorensen, E. J. J. Am. Chem. Soc. 2003, 125, 5393. https://doi.org/10.1021/ja021472b
  10. Huckins, J. R.; De Vicente, J.; Rychnovsky, S. D. Org. Lett. 2007, 9, 4757. https://doi.org/10.1021/ol7020934
  11. Gopalarathnam, A.; Nelson, S. G. Org. Lett. 2006, 8, 7. https://doi.org/10.1021/ol051861l
  12. Schuppan, J.; Ziemer, B.; Koert, U. Tetrahedron Lett. 2000, 41, 621. https://doi.org/10.1016/S0040-4039(99)02134-6
  13. Gomez-Monterrey, I, M.; Campiglia, P.; Bertamino, A.; Aquino, C.; Mazzoni, O.; Diurno, M. V.; Iacovino, R.; Saviano, M.; Sala, M.; Novellino, E.; Grieco, P. Eur. J.Org. Chem. 2008, 11, 1983.
  14. Gomez-Monterrey, I. M.; Campiglia, P.; Bertamino, A.; Mazzoni, O.; Diurno, M. V.; Novellino, E.; Grieco, P. Tetrahedron 2006, 62, 8083. https://doi.org/10.1016/j.tet.2006.06.010
  15. Grieco, P.; Campiglia, P.; Gomez-Monterrey, I.; Novellino, E. Tetrahedron Lett. 2002, 43, 6297. https://doi.org/10.1016/S0040-4039(02)01404-1
  16. Wu, Y.; Xu, J.-C. Tetrahedron 2001, 57, 8107. https://doi.org/10.1016/S0040-4020(01)00789-X
  17. Owens, T. D.; Araldi, G.-L.; Nutt, R. F.; Semple, J. E. Tetrahedron Lett. 2001, 42, 6271. https://doi.org/10.1016/S0040-4039(01)01287-4
  18. Deagostino, A.; Karini, P.; Occhiato, E. G.; Pizzuto, L.; Prandi, C.; Venturello, P. J. Org. Chem. 2008, 73, 1941. https://doi.org/10.1021/jo7024898
  19. Martinelli, J. R.; Freckmann, D. M. M.; Buchwald, S. L. Org. Lett. 2006, 8, 4843. https://doi.org/10.1021/ol061902t
  20. Aungst, R. A.; Funk, R. L. J. Am. Chem. Soc. 2001, 123, 9455. https://doi.org/10.1021/ja011470b
  21. Murakami, M.; Hoshino, Y.; Ito, H.; Ito, Y. Chem. Lett. 1998, 163.
  22. Nemoto, H.; Ma, R.; Moriguchi, H.; Kawamura, T.; Kamiya, M.; Shibuya, M. J. Org. Chem. 2007, 72, 9850. https://doi.org/10.1021/jo701859a
  23. Lee, J. I. Bull. Korean Chem. Soc. 2007, 28, 695. https://doi.org/10.5012/bkcs.2007.28.4.695
  24. Gibson, C. L.; Handa, S. Tetrahedron-Asymmetry 1996, 7, 1281. https://doi.org/10.1016/0957-4166(96)00144-9
  25. Braun, M.; Waldmuller, D. Synthesis 1989, 856.
  26. Dechantsreiter, M. A.; Burkhart, F.; Kessler, H. Tetrahedron Lett. 1998, 39, 253. https://doi.org/10.1016/S0040-4039(97)10566-4
  27. Oppolzer, W.; Cunningham, A. F. Tetrahedron Lett. 1986, 27, 5467. https://doi.org/10.1016/S0040-4039(00)85239-9
  28. Katritzky, A. R.; Yang, H.; Zhang, S.; Wang, M. ARKIVOC 2002, 39.
  29. Shreder, K.; Zhang, L.; Goodman, M. Tetrahedron Lett. 1998, 39, 221. https://doi.org/10.1016/S0040-4039(97)10530-5
  30. Maugras, I.; Poncet, J.; Jouin, P. Tetrahedron 1990, 46, 2807. https://doi.org/10.1016/S0040-4020(01)88373-3
  31. De Luca, L.; Gaicomelli, G.; Taddei, M. J. Org. Chem. 2001, 66, 2534. https://doi.org/10.1021/jo015524b
  32. Lee, J. I.; Park, H. Bull. Korean. Chem. Soc. 2001, 22, 421.
  33. Sibi, M. P.; Stressman, C. C.; Schultz, J. A.; Christensen, J. W.; Lu, J.; Marvin, M. Synth. Commun. 1995, 25, 1255. https://doi.org/10.1080/00397919508012689
  34. White, J. M.; Tunoori, A. R.; Turunen, B. J.; Georg, G. I. J. Org. Chem. 2008, 73, 1941. https://doi.org/10.1021/jo7024898
  35. Tunoori, A. R.; White, J. M.; Georg, G. I. Org. Lett. 2000, 2, 4091. https://doi.org/10.1021/ol000318w
  36. Han, K.-D.; Kim, M. Lett. Org. Chem. 2007, 4, 20. https://doi.org/10.2174/157017807780037441
  37. Woo, J. C. S.; Fenster, E. Dake, G. R. J. Org. Chem. 2004, 69, 8984. https://doi.org/10.1021/jo048385h
  38. Kim, M.; Lee, H.; Han, K.-J.; Kay, K.-Y. Synth. Commun. 2003, 33, 4013. https://doi.org/10.1081/SCC-120026336
  39. Davies, D. T.; O'Hanlon, P. J. Synth. Commun. 1988, 18, 2273. https://doi.org/10.1080/00397918808082370
  40. Jang, D. O.; Park, D. J.; Kim, J. Tetrahedron Lett. 1999, 40, 5323. https://doi.org/10.1016/S0040-4039(99)00967-3
  41. Bailen, M. A.; Chinchilla, R; Dodsworth, D. J.; and Najera, C. Tetrahedron Lett. 2001, 42, 5013. https://doi.org/10.1016/S0040-4039(01)00923-6
  42. Sureshbabu, V. V.; Hemantha, H. P. ARKIVOC 2008, 243.

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