DOI QR코드

DOI QR Code

Baylis-Hillman Reaction of Isatin Derivatives: Isatins as a New Entry for the Baylis-Hillman Reaction


Abstract

Keywords

References

  1. Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001. https://doi.org/10.1016/0040-4020(96)00154-8
  2. Ciganek, E. Organic Reactions; John Wiley & Sons: New York, 1997; Vol. 51, pp 201-350.
  3. Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653. https://doi.org/10.1016/S0040-4020(01)86168-8
  4. Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049. https://doi.org/10.1002/1521-3773(20000901)39:17<3049::AID-ANIE3049>3.0.CO;2-5
  5. Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627. https://doi.org/10.2174/1385272023374094
  6. Hill, J. S.; Isaacs, N. S. Tetrahedron Lett. 1986, 27, 5007. https://doi.org/10.1016/S0040-4039(00)85119-9
  7. Hill, J. S.; Isaacs, N. S. J. Chem. Res. (M) 1988, 1, 2641.
  8. Hill, J. S.; Isaacs, N. S. J. Chem. Res. (S) 1988, 330.
  9. Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 2000, 757.
  10. Alcaide, B.; Almendros, P.; Aragoncillo, C. Tetrahedron Lett. 1999, 40, 7537. https://doi.org/10.1016/S0040-4039(99)01527-0
  11. Basavaiah, D.; Bharathi, T. K.; Gowriswari, V. V. L. Tetrahedron Lett. 1987, 28, 4351. https://doi.org/10.1016/S0040-4039(00)96506-7
  12. Strunz, G. M.; Bethell, R.; Sampson, G.; White, P. Can. J. Chem. 1995, 73, 1666. https://doi.org/10.1139/v95-206
  13. Basavaiah, D.; Muthukumaran, K.; Sreenivasulu, B. Synlett 1999, 1249.
  14. Vojkovsky, T. Abstr. 211th Meeting of the American Chemical Society, New Oreleans, 1996, ORGN 288.
  15. The preliminary results of ours have been reported earlier in the 88th Annual Meeting of the Korean Chemical Society, S23P80 (October 19, 2001).
  16. Garden, S. J.; Skakle, J. M. S. Tetrahedron Lett. 2002, 43, 1969. https://doi.org/10.1016/S0040-4039(02)00160-0
  17. Kim, J. N.; Lee, H. J.; Lee, K. Y.; Gong, J. H. Synlett 2002, 173.
  18. Gong, J. H.; Im, Y. J.; Lee, K. Y.; Kim, J. N. Tetrahedron Lett. 2002, 43, 1247. https://doi.org/10.1016/S0040-4039(01)02344-9
  19. Chung, Y. M.; Gong, J. H.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2001, 42, 9023. https://doi.org/10.1016/S0040-4039(01)01971-2
  20. Kim, J. N.; Kim, H. S.; Gong, J. H.; Chung, Y. M. Tetrahedron Lett. 2001, 42, 8341. https://doi.org/10.1016/S0040-4039(01)01791-9
  21. Kim, J. N.; Im, Y. J.; Gong, J. H.; Lee, K. Y. Tetrahedron Lett. 2001, 42, 4195. https://doi.org/10.1016/S0040-4039(01)00687-6
  22. Kim, J. N.; Lee, H. J.; Lee, K. Y.; Kim, H. S. Tetrahedron Lett. 2001, 42, 3737. https://doi.org/10.1016/S0040-4039(01)00552-4
  23. Kim, H. S.; Kim, T. Y.; Lee, K. Y.; Chung, Y. M.; Lee, H. J.; Kim, J. N. Tetrahedron Lett. 2000, 41, 2613. https://doi.org/10.1016/S0040-4039(00)00229-X
  24. Kim, J. N.; Lee, K. Y.; Kim, H. S.; Kim, T. Y. Org. Lett. 2000, 2, 343. https://doi.org/10.1021/ol9903741
  25. Garden, S. J.; Torres, J. C.; Ferreira, A. A.; Silva, R. B.; Pinto, A. C. Tetrahedron Lett. 1997, 38, 1501. https://doi.org/10.1016/S0040-4039(97)00140-8
  26. Kawasaki, T.; Ohtsuka, H.; Chien, C.-S.; Omata, M.; Sakamoto, M. Chem. Pharm. Bull. 1987, 35, 1339. https://doi.org/10.1248/cpb.35.1339
  27. Desarbre, E.; Savelon, L.; Cornec, O.; Merour, J. Y. Tetrahedron 1996, 52, 2983. https://doi.org/10.1016/0040-4020(96)00001-4
  28. Angell, E. C.; Black, D. St C.; Kumar, N. Magn. Reson. Chem. 1992, 30, 1. https://doi.org/10.1002/mrc.1260300102
  29. Meyer, F. J. Chem. Ber. 1966, 99, 3060. https://doi.org/10.1002/cber.19660990942
  30. Popp, F. D.; Piccirilli, R. M. J. Heterocyclic Chem. 1971, 8, 473. https://doi.org/10.1002/jhet.5570080319
  31. de Mayo, P.; Ryan, J. J. Can. J. Chem. 1967, 45, 2117. https://doi.org/10.1139/v67-343
  32. Bergman, J.; Carlsson, R.; Lindstrom, J.-O. Tetrahedron Lett. 1976, 3611.

Cited by

  1. Hydroxyalkylation of Conjugated Nitroalkenes with Activated Nonenolizable Carbonyl Compounds vol.8, pp.6, 2006, https://doi.org/10.1021/ol060041l
  2. Isatins As Privileged Molecules in Design and Synthesis of Spiro-Fused Cyclic Frameworks vol.112, pp.11, 2012, https://doi.org/10.1021/cr300135y
  3. C–H Functionalization vol.14, pp.3, 2012, https://doi.org/10.1021/ol2030982
  4. Aqueous Morita–Baylis–Hillman Reaction of Unprotected Isatins with Cyclic Enones vol.15, pp.22, 2013, https://doi.org/10.1021/ol4029034
  5. -Glyoxylamino Acid Esters vol.2013, pp.2090-9071, 2013, https://doi.org/10.1155/2013/901745
  6. Direct asymmetric aldol addition–isomerization of α,β-unsaturated γ-butyrolactam with aryl α-ketoesters: synthesis of MBH-type products vol.49, pp.32, 2013, https://doi.org/10.1039/c3cc40717a
  7. Isatin as a Strategic Motif for Asymmetric Catalysis vol.5, pp.8, 2013, https://doi.org/10.1002/cctc.201300050
  8. ) – mediated regioselective β-cross-coupling aldol type addition reaction of activated alkenes with isatins/isatinimines in aqueous media vol.5, pp.64, 2015, https://doi.org/10.1039/C5RA07216F
  9. )-trione Derivatives vol.98, pp.10, 2015, https://doi.org/10.1002/hlca.201500106
  10. ) – catalyzed α-cross-coupling aldol type addition reaction of activated olefins with isatins vol.6, pp.3, 2016, https://doi.org/10.1039/C5RA14714J
  11. Morita-Baylis-Hillman Reactions Between Conjugated Nitroalkenes or Nitrodienes and Carbonyl Compounds vol.2009, pp.24, 2009, https://doi.org/10.1002/ejoc.200900475
  12. Baylis—Hillman Reaction of Isatin Derivatives: Isatins as a New Entry for the Baylis—Hillman Reaction. vol.34, pp.15, 2002, https://doi.org/10.1002/chin.200315120
  13. Synthesis of 3-Aryl-3-hydroxypyrrolidin-2-ones and 2-Benzyl-9b-hydroxy-3,3a,5,9b-tetrahydro-2H-pyrrolo[3,4-c]quinoline-1,4-dione Derivatives from the Baylis-Hillman Adducts of Isatins vol.27, pp.8, 2002, https://doi.org/10.5012/bkcs.2006.27.8.1133
  14. Synthesis of 3-aryl-3-hydroxypyrrolidin-2-ones and 2-benzyl-9b-hydroxy-3,3a,5,9b-tetrahydro-2H-pyrrolo[3,4-c]quinoline-1,4-dione derivatives from the Baylis–Hillman adducts of isatins vol.47, pp.20, 2006, https://doi.org/10.1016/j.tetlet.2006.03.074
  15. Construction of Chiral Quaternary Carbon through Morita–Baylis–Hillman Reaction: An Enantioselective Approach to 3‐Substituted 3‐Hydroxyoxindole Derivatives vol.16, pp.46, 2002, https://doi.org/10.1002/chem.201002240
  16. Catalytic asymmetric synthesis of 3-hydroxyl-2-oxindoles via enantioselective Morita–Baylis–Hillman reaction of isatins vol.67, pp.16, 2002, https://doi.org/10.1016/j.tet.2011.02.045
  17. Microwave irradiation: synthesis and characterization of α-ketoamide and bis (α-ketoamide) derivatives via the ring opening of N -acetylisatin vol.8, pp.None, 2002, https://doi.org/10.1186/1752-153x-8-27
  18. Synthesis of Substituted Isatins from the MBH Adduct of 1,5,6-Trisubstituted Isatins Using (2,4-Dinitrophenyl)hydrazine and K-10 Clay Explored as Protection-Deprotection Chemistry vol.4, pp.5, 2002, https://doi.org/10.1021/acsomega.9b01002
  19. Stereoselective synthesis and discovery of novel spirooxindolopyrrolidine engrafted indandione heterocyclic hybrids as antimycobacterial agents vol.110, pp.None, 2002, https://doi.org/10.1016/j.bioorg.2021.104798