Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

A Novel Synthesis of Ketones Using 4,6-Pyrimidyl Diesters

  • Lee, Jae-In (Department of Chemistry/Plant Resources Research Institute, College of Natural Science, Duksung Women's University)
  • Published : 2007.05.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. O'neill, B. T. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U. K., 1991; Vol. 1, p 397
  2. Walter, D. S. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Ed.; Elsevier Science Ltd.: Oxford, U. K., 1995; Vol. 3, p 277
  3. Aldabbagh, F. In Comprehensive Organic Functional Group Transformations II; Katritzky, A. R., Ed.; Elsevier Ltd.: Oxford, U. K., 2005; Vol. 3, p 267
  4. Mukaiyama, T.; Araki, M.; Takei, H. J. Am. Chem. Soc. 1973, 95, 4763 https://doi.org/10.1021/ja00795a055
  5. Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647 https://doi.org/10.1016/S0040-4039(01)83003-3
  6. Vazquez, J.; Albericio, F. Tetrahedron Lett. 2002, 43, 7499 https://doi.org/10.1016/S0040-4039(02)01805-1
  7. Araki, M.; Sakata, S.; Takei, H.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1974, 47, 1777 https://doi.org/10.1246/bcsj.47.1777
  8. Meyers, A. I.; Comins, D. L. Tetrahedron Lett. 1978, 19, 5179 https://doi.org/10.1016/S0040-4039(01)85843-3
  9. Abe, K.; Sato, T.; Nakamura, N.; Sakan, T. Chem. Lett. 1977, 645
  10. Heras, M. A.; Molina, A.; Vaquero, J. J.; Navio, J. L. G.; Alvarez-Builla, J. J. Org. Chem. 1993, 58, 5862
  11. Heras, M. A.; Vaquero, J. J.; Navio, J. L. G.; Alvarez-Builla, J. Tetrahedron 1996, 52, 14297
  12. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815 https://doi.org/10.1016/S0040-4039(01)91316-4
  13. Sibi, M. P. Org. Prep. Proced. Int. 1993, 25, 15 https://doi.org/10.1080/00304949309457931
  14. Liu, J.; Ikemoto, N.; Petrillo, D.; Armstrong, J. D. Tetrahedron Lett. 2002, 43, 8223 https://doi.org/10.1016/S0040-4039(02)02031-2
  15. Olah, G. A.; Prakash, G. K. S.; Arvanaghi, M. Synthesis 1984, 228
  16. Comins, D. L.; Hong, H. J. Am. Chem. Soc. 1991, 113, 6672 https://doi.org/10.1021/ja00017a047
  17. Wattanasin, S.; Kathawala, F. G. Tetrahedron Lett. 1984, 25, 811 https://doi.org/10.1016/S0040-4039(01)80033-2
  18. Creary, X. J. Org. Chem. 1987, 52, 5026 https://doi.org/10.1021/jo00231a036
  19. Yang, B. Q.; Qiang, J. L.; Bai, Y. J.; Lu, J.; Shi, Z. Chinese J. Chem. 2003, 21, 1210 https://doi.org/10.1002/cjoc.20030210921
  20. Duplais, C.; Bures, F.; Sapountzis, I.; Korn, T. J.; Cahiez, G.; Knochel, P. Angew. Chem. Int. Ed. 2004, 43, 2968 https://doi.org/10.1002/anie.200453696
  21. Itsuno, S.; Miyazaki, K.; Ito, K. Tetrahedron Lett. 1986, 27, 3033 https://doi.org/10.1016/S0040-4039(00)84709-7
  22. Weiberth, F. J.; Hall, S. S. J. Org. Chem. 1987, 52, 3901 https://doi.org/10.1021/jo00226a033
  23. Strekowski, L.; Wydra, R. L.; Cegla, M. T.; Czarny, A.; Patterson, S. J. Org. Chem. 1989, 54, 6120 https://doi.org/10.1021/jo00287a028

Cited by

  1. Catalytic Decarboxylative Cross-Ketonisation of Aryl- and Alkylcarboxylic Acids using Magnetite Nanoparticles vol.353, pp.1, 2010, https://doi.org/10.1002/adsc.201000429
  2. Alkali-Metal Ion Catalysis in Alkaline Ethanolysis of 2-Pyridyl Benzoate and Benzyl 2-Pyridyl Carbonate: Effect of Modification of Nonleaving Group from Benzoyl to Benzyloxycarbonyl vol.33, pp.2, 2012, https://doi.org/10.5012/bkcs.2012.33.2.519
  3. Kinetics and Reaction Mechanism of Aminolyses of Benzyl 2-Pyridyl Carbonate and t-Butyl 2-Pyridyl Carbonate in Acetonitrile vol.33, pp.5, 2012, https://doi.org/10.5012/bkcs.2012.33.5.1547
  4. Kinetics and Reaction Mechanism of Aminolyses of Benzyl 2-Pyridyl Carbonate and t-Butyl 2-Pyridyl Carbonate: Effect of Nonleaving Group on Reactivity and Reaction Mechanism vol.33, pp.5, 2012, https://doi.org/10.5012/bkcs.2012.33.5.1551
  5. Alkali-Metal Ion Catalysis in Nucleophilic Substitution Reactions of 5-Nitro-8-quinolyl Picolinate with Alkali Metal Ethoxides: Effect of Modification of Nonleaving Group from Benzoyl to Picolinyl on Reactivity and Transition State Structure vol.35, pp.5, 2014, https://doi.org/10.5012/bkcs.2014.35.5.1506
  6. Ar Reactions of 1-Halo-2,4-dinitrobenzenes with Alkali-Metal Ethoxides: Differential Stabilization of Ground State and Transition State Determines Alkali-Metal Ion Catalysis or Inhibition vol.36, pp.7, 2015, https://doi.org/10.1002/bkcs.10344
  7. A Novel Synthesis of Ketones Using 4,6-Pyrimidyl Diesters. vol.38, pp.38, 2007, https://doi.org/10.1002/chin.200738054
  8. Metal Ion Catalysis in Nucleophilic Displacement Reactions of 2-Pyridyl X-Substituted Benzoates with Potassium Ethoxide in Anhydrous Ethanol vol.31, pp.12, 2007, https://doi.org/10.5012/bkcs.2010.31.12.3543
  9. A Kinetic Study on Aminolysis of 2-Pyridyl X-Substituted Benzoates: Effect of Changing Leaving Group from 4-Nitrophenolate to 2-Pyridinolate on Reactivity and Mechanism vol.31, pp.12, 2010, https://doi.org/10.5012/bkcs.2010.31.12.3588
  10. 6-Methyl-2,4-pyrimidyl Diesters. A Highly Efficient Acylating Agent for the Synthesis of Unsymmetrical Ketones vol.31, pp.3, 2007, https://doi.org/10.5012/bkcs.2010.31.03.749
  11. Effect of Alkali Metal Ions on Alkaline Ethanolysis of 2-Pyridyl and 4-Pyridyl Benzoates in Anhydrous Ethanol vol.31, pp.10, 2007, https://doi.org/10.5012/bkcs.2010.31.10.2929
  12. A Novel Synthesis of Carboxylic Esters from 2-Methyl-4,6-pyrimidyl Dicarbonates and Grignard Reagents vol.32, pp.5, 2007, https://doi.org/10.5012/bkcs.2011.32.5.1765
  13. Kinetics and Reaction Mechanism for Aminolysis of Benzyl 4-Pyridyl Carbonate in H2O: Effect of Modification of Nucleofuge from 2-Pyridyloxide to 4-Pyridyloxide on Reactivity and Reaction Me vol.33, pp.7, 2007, https://doi.org/10.5012/bkcs.2012.33.7.2269
  14. Aminolysis of Benzyl 4-Pyridyl Carbonate in Acetonitrile: Effect of Modification of Leaving Group from 2-Pyridyloxide to 4-Pyridyloxide on Reactivity and Reaction Mechanism vol.33, pp.8, 2007, https://doi.org/10.5012/bkcs.2012.33.8.2719
  15. A Kinetic Study on Aminolysis of t-Butyl 4-Pyridyl Carbonate and Related Compounds: Effect of Leaving and Nonleaving Groups on Reaction Mechanism vol.33, pp.9, 2007, https://doi.org/10.5012/bkcs.2012.33.9.2971
  16. An Efficient Synthesis of 1-Alkyl-2-phenyl-4-quinolones from 2-Halobenzoic Acids vol.34, pp.10, 2007, https://doi.org/10.5012/bkcs.2013.34.10.3117
  17. Synthesis and Versatile Utilization of 2‐PYRIDYL and PYRIMIDYL‐RELATED Reagents vol.41, pp.7, 2007, https://doi.org/10.1002/bkcs.12061