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A Novel Synthesis of N-Methoxy-N-methylamides from 4,6-Pyrimidyl Urethane and Grignard Reagents

  • Lee, Jae-In (Department of Chemistry, College of Natural Science, Duksung Women's University)
  • Published : 2007.04.20
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Abstract

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References

  1. For a review on the application of N-methoxy-N-methylamides: Sibi, M. P. Org. Prep. Proced. Int. 1993, 25, 15
  2. Sibi, M. P.; Marvin, M.; Sharma, R. J. Org. Chem. 1995, 60, 5016 https://doi.org/10.1021/jo00121a021
  3. Jackson, M. M.; Leverett, C.; Toczko, J. F.; Roberts, J. C. J. Org. Chem. 2002, 67, 5032 https://doi.org/10.1021/jo025682i
  4. Einhorn, J.; Einhorn, C.; Luche, J. L. Synth. Comm. 1990, 20, 1105 https://doi.org/10.1080/00397919008052817
  5. Banwell, M.; Smith, J. Synth. Comm. 2001, 31, 2011 https://doi.org/10.1081/SCC-100104418
  6. Poss, M. A.; Reid, J. A. Tetrahedron Lett. 1992, 33, 1411 https://doi.org/10.1016/S0040-4039(00)91634-4
  7. Lee, J. I.; Park, H. Bull. Korean Chem. Soc. 2001, 22, 421
  8. Brenner-WeiB, G.; Giannis, A.; Sandhoff, K. Tetrahedron 1992, 48, 5855
  9. Sibi, M. P.; Stessman, C. C.; Schultz, J. A.; Christensen, J. W.; Lu, J.; Marvin, M. Synth. Comm. 1995, 25, 1255 https://doi.org/10.1080/00397919508012689
  10. D'Aniello, F.; Mann, A. J. Org. Chem. 1996, 61, 4870 https://doi.org/10.1021/jo9605004
  11. Shreder, K.; Zhang, L.; Goodman, M. Tetrahedron Lett. 1998, 39, 221 https://doi.org/10.1016/S0040-4039(97)10530-5
  12. Wen, J. J.; Crews, C. M. Tetrahedron: Asymmetry 1998, 9, 1855 https://doi.org/10.1016/S0957-4166(98)00183-9
  13. Luca, L. D.; Giacomelli, G.; Taddei, M. J. Org. Chem. 2001, 66, 2534 https://doi.org/10.1021/jo015524b
  14. Hioki, K.; Kobayashi, H.; Ohkihara, R.; Tani, S.; Kunishima, M. Chem. Pharm. Bull. 2004, 52, 470 https://doi.org/10.1248/cpb.52.470
  15. Raghuram, T.; Vijaysaradhi, S.; Singh, I.; Singh, J. Synth. Comm. 1999, 29, 3215 https://doi.org/10.1080/00397919908085946
  16. Lucet, D.; Gall, T. L.; Mioskowski, C.; Ploux, O.; Marquet, A. Tetrahedron: Asymmetry 1996, 7, 985 https://doi.org/10.1016/0957-4166(96)00098-5
  17. Falorni, M.; Giacomelli, G.; Spanedda, A. M. Tetrahedron: Asymmetry 1998, 9, 3039 https://doi.org/10.1016/S0957-4166(98)00305-X
  18. Murray, A.; Proctor, G. R. Tetrahedron Lett. 1995, 36, 291 https://doi.org/10.1016/0040-4039(94)02233-2
  19. Irako, N.; Hamada, Y.; Shioiri, T. Tetrahedron 1992, 48, 7251 https://doi.org/10.1016/S0040-4020(01)88264-8
  20. Dechantsreiter, M. A.; Burkhart, F.; Kessler, H. Tetrahedron Lett. 1998, 39, 253 https://doi.org/10.1016/S0040-4039(97)10566-4
  21. Woo, J. C. S.; Fenster, E.; Dake, G. R. J. Org. Chem. 2004, 69, 8984 https://doi.org/10.1021/jo048385h
  22. Aidhen, I. S.; Ahuja, J. R. Tetrahedron Lett. 1992, 33, 5431 https://doi.org/10.1016/S0040-4039(00)79113-1
  23. Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461
  24. Iseki, K.; Asada, D.; Kuroki, Y. J. Fluorine Chem. 1999, 97, 85 https://doi.org/10.1016/S0022-1139(99)00033-0
  25. Davis, F. A.; Kasu, P. V. N. Tetrahedron Lett. 1998, 39, 6135 https://doi.org/10.1016/S0040-4039(98)01296-9
  26. Paquette, L. A.; Zuev, D. Tetrahedron Lett. 1997, 38, 5115 https://doi.org/10.1016/S0040-4039(97)01140-4
  27. Lee, J. I.; Jung, H. J. J. Korean Chem. Soc. 2005, 49, 609 https://doi.org/10.5012/jkcs.2005.49.6.609
  28. Lee, J. I.; Park, H. Bull. Korean Chem. Soc. 2002, 23, 521 https://doi.org/10.5012/bkcs.2002.23.3.521

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