78
Views
19
CrossRef citations to date
0
Altmetric
Original Articles

THE LATERAL METALATION OF ISOXAZOLES. A REVIEW

&
Pages 515-556 | Received 19 Jun 1992, Published online: 18 Feb 2009

References

  • Gschwend , H. W. and Rodriguez , H. R. 1979 . Org. React. , 26 : 1 Lateral metalation is discussed briefly under the heading of “Acidic Groups”, p. 16.
  • Beak , P. and Brown , R. A. 1982 . J. Org. Chem. , 47 : 34 b) F. M. Hauser, R. P. Rhee, R. Prasanna, S. M. Weinreb and J. H. Dodd, Synthesis, 72(1980); c) R. J. Mills and V. Snieckus, J. Org. Chem., 48, 1565(1983); d) D. L. Comins and J. D. Brown, ibid., 49, 1078(1984).
  • Kelly , T. R. , Ohashi , N. , Armstrong-Chong , R. J. and Bell , S. H. 1986 . J. Am. Chem. Soc. , 108 : 7100 Although in this paper lateral metalation did not succeed as planned, it nevertheless represents a good lead reference on the topic.
  • Kaiser , E. M. 1983 . Tetrahedron , 39 : 2055
  • Grunanger , P. and Vita-Finzi , P. 1990 . “Isoxazoles” , New York : John Wiley & Sons, Inc. . This text contains a review of the literature through 1984, with some 1985 references; b) S. A. Lang and Y.-i Lin, Comprehensive Heterocyclic Chemistry Potts, K. T., Ed. Pergamon Press, NY 6, 1 (1984); c) B. J. Wakefield and D. J. Wright, Adv. Het. Chem., 25, 147(1979); d) N. K. Kochetkov and S. D. Sokolov, Adv. Het. Chem., 2, 365(1963).
  • Baraldi , P. G. , Barco , A. , Benett , S. and Pollini , G. P. 1987 . Synthesis , : 857 For a review on the use of isoxazoles in natural products synthesis, see
  • Stork , G. , Danishefsky , S. and Ohashi , M. 1967 . J. Am. Chem. Soc. , 89 : 5459 b) G. Stork and J. E. McMurry, ibid., 89, 5463(1967); c) G. Stork and J. E. McMurry, ibid., 89, 5464(1967); d) J. E. McMurry, Org. Synth., Coll. Vol. VI, 781(1988); e) For an asymmetric isoxazole annulation, see: B. E. Marron, L. Schlicksupp and N. R. Natale, J. Heterocycl. Chem., 25, 1067(1988).
  • Mirzaei , Y. R. 1990 . Ph. D. Thesis University of Idaho . Reviews cited in references 1a and 1b contain sections on isoxazole with interesting biological activity, for updates, see: b) B. M. Mallet, M. S. Thesis, University of Idaho, 1988.
  • Doyle , F. P. , Long , A. A. W. , Nayler , J. H. C. and Stove , E. R. 1961 . Nature , 192 : 1183 b) B. C. Rudy and B. Z. Senkowski, in Analytical Profiles of Drug Substances, K. Florey, Ed. Academic Press, New York. 1973, Vol. 2, pp. 467–86.
  • Smith , T. J. , Kremer , M. J. , Luo , M. , Vriend , G. , Arnold , E. , Kamer , G. , Rossman , M. G. , McKinlay , M. A. and Diana , G. D. 1986 . Science , 26 : 1286 b) M. A. McKinlay and G. D. Diana, in The Molecular Basis of Viral Replication, R. Bercoff, Ed. Plenum Press, NY Chapter 2(1987).
  • Natale , N. R. , Triggle , D. J. , Palmer , R. B. , Lefler , B. J. and Edwards , W. D. 1990 . J. Med. Chem. , 33 : 2255 b) J. I. McKenna, L. Schlicksupp, N. R. Natale, B. E. Maryanoff, S. F. Flaim and R. D. Willett, J. Med. Chem., 31, 473(1988).
  • Woodward , R. B. and Olofson , R. A. 1988 . Org. Synth. Coll. , Vol. VI : 263 b) K. Llamas, M. Owens, R. L. Blakeley and B. Zerner, J. Am. Chem. Soc., 108, 5543(1986).
  • Kemp , D. S. and Hoyng , C. F. 1975 . Tetrahedron Lett. , : 4625
  • Olofson , R. A. , Morrison , D. S. and Banerji , A. 1984 . J. Org. Chem. , 49 : 2653
  • Harris , T. M. , Harris , C. M. , Oster , T. A. , Brown , L. E. and Lee , J. Y.-C. 1988 . J. Am. Chem. Soc. , 110 : 6180
  • Hoskin , D. H. and Olofson , R. A. 1982 . J. Org. Chem. , 47 : 5222 b) G. N. Barber and R. A. Olofson, ibid., 43, 3015(1978); c) C. Beam, M. C. D. Dyer, R. A. Schwarz and C. R. Hauser, ibid., 35, 1806(1970); d) A. M. Huff, H. L. Hall, M. J. Smith, S. A. O'Grady, F. C. Waters, R. W. Fengl, J. A. Welsh and C. F. Beam, J. Heterocyclic Chem., 22, 501(1985).
  • Micetich , R. G. and Chin , C. C. 1970 . Can J. Chem. , 48 : 1371 b) A. Albertola, A. P. Serrano, M. T. Rodriquez and C. Orozco, Heterocycles, 29, 667(1989); c) A. Alberola, L. Calvo, T. Rodriguez, C. Sanudo, J. Heterocyclic Chem. 29, 445(1992).
  • Pepino , R. , Ricci , A. , Taddei , M. , Tedaschi , P. and Seconi , G. 1982 . J. Organomet. Chem. , 231 : 91
  • Alberola , A. , Antolin , L. F. , Gonzalez , A. , Laguna , M. A. and Pulido , F. J. 1988 . J. Chem. Soc. Perkin Trans I , : 791
  • Adachi , T. , Harada , K. , Miyazaki , R. and Kano , H. 1974 . Chem. Pharm. Bull. Jpn , 22 : 61
  • Freeman , J. P. 1983 . Chem. Rev. , 83 : 241
  • Alberola , A. , Gonzalez , A. M. , Laguna , M. A. and Pulido , F. J. 1986 . Synth. Commun. , 16 : 673
  • Bowden , K. , Crank , G. and Ross , W. J. 1968 . J. Chem. Soc. , : 172
  • Gainer , J. , Howarth , G. A. , Hoyle , W. , Roberts , S. M. and Suzchitsky , H. 1976 . J. Chem. Soc. , : 994
  • Micetich , R. G. , Shaw , C. C. , Hall , T. W. , Spevak , P. and Bains , B. K. 1985 . Heterocycles , 23 : 585
  • Oster , T. A. and Harris , T. M. 1983 . J. Org. Chem. , 48 : 4307
  • Kashima , C. , Yamamoto , Y. and Tsuda , Y. 1977 . Heterocycles , 6 : 805
  • Brunnelle , D. J. 1981 . Tetrahedron Lett. , : 3699
  • Schlicksupp , L. and Natale , N. R. 1987 . J. Heterocycl. Chem. , 24 : 1345
  • Polo , C. , Ramos , V. , Torroba , T. , Bossio , R. , Marcaccini , S. and Pepino , R. 1990 . Heterocycles , 31 : 811 (b) J.-C. Cherton, M. Lanson, D. Ladjama, N. Lefebvre, Z. Vossough and J.-J. Basselier, Can. J. Chem., 69, 625(1991).
  • Micetich , R. 1970 . Can J. Chem. , 48 : 2006
  • Oliver , J. E. , Waters , R. M. and Lusby , W. R. 1989 . J. Org. Chem. , 54 : 4970
  • Ranganathan , S. , Ranganathan , P. V. and Ramachandran , P. V. 1981 . Tetrahedron , 24 : 4171
  • Diana , G. D. , McKinlay , M. A. , Otto , M. J. , Akullian , V. and Oglesby , C. 1985 . J. Med. Chem. , 28 : 1906 b) G. D. Diana, M. A. McKinlay, C. J. Brisson, E. S. Zalay and J. V. Miralles, ibid., 28, 748(1985).
  • Yokoyama , M. , Tsuji , K. and Kushida , M. 1986 . J. Chem. Soc. Perkin Trans. I , : 67
  • Sakakibara , T. , Kume , T. , Shimohara , K. , Fujishima , H. , Hara , S. and Shimoda , T. 1990 . Heterocycles , 31 : 459
  • Natale , N. R. and Niou , C. S. 1984 . Tetrahedron Lett. , 25 : 3943
  • Natale , N. R. , McKenna , J. I. , Niou , C. S. , Borth , M. and Hope , H. 1985 . J. Org. Chem. , 50 : 5660
  • Niou , C. S. and Natale , N. R. 1986 . Heterocycles , 24 : 401
  • Natale , N. R. Unpublished observations with B. J. Lefler. Twenty grams (0. 103 mole) could be monoalkylated in 1 L of THF in 92% yield (average of three runs).
  • Xia , X. B. , Knerr , G. and Natale , N. R. in press . J. Heterocycl. Chem. ,
  • Nadelson , J. US Patent . 4,122,182 . Chem. Abstr. 90, 203873t (1979).
  • Franke , A. , Frickel , F. F. , Gries , J. , Lenke , D. , Schlecker , R. and Thieme , P. D. 1981 . J. Med. Chem. , 24 : 1460
  • DeShong , P. , Cipollina , J. A. and Lowmaster , N. K. 1988 . J. Org. Chem. , 53 : 1356
  • Collington , E. W. , Knight , J. G. , Wallis , C. J. and Warren , S. 1989 . Tetrahedron Lett. , 30 : 877
  • Balu , M. P. , Pooranchand , D. , Ila , H. and Junjappa , H. 1988 . Tetrahedron Lett. , 29 : 501
  • Xia , X. B. , Munsey , M. S. , Du , H. , Wai , C. M. and Natale , N. R. 1991 . Heterocycles , 32 : 711
  • Gilbreath , S. G. , Harris , C. M. and Harris , T. M. 1988 . J. Am. Chem. Soc. , 110 : 6172
  • Natale , N. R. , Yocklovich , S. G. and Mallet , B. M. 1986 . Heterocycles , 24 : 2178
  • Alreja , B. D. , Kattige , L. S. , Lal , B. and de Souza , N. J. 1986 . Heterocycles , 24 : 1637
  • Madsen , U. , Brehm , L. and Krogsgaard-Larsen , P. 1988 . J. Chem. Soc. Perkin Trans. I , : 359
  • Mirzaei , Y. R. , Balasubramaniam , T. N. , Lefler , B. J. and Natale , N. R. 1990 . J. Heterocycl. Chem. , 27 : 2001
  • Davis , F. A. and Sheppard , A. C. 1989 . Tetrahedron , 45 : 5703
  • Nesi , R. , Ricci , A. , Taddei , M. , Tedeschi , P. and Seconi , G. 1980 . J. Organomet. Chem. , 195 : 275
  • Borth , M. , Bowles , K. D. , Schlicksupp , L. and Natale , N. R. 1987 . J. Organomet. Chem. , 331 : 1
  • Balasubramaniam , T. N. , Mirzaei , Y. R. and Natale , N. R. 1990 . Synthesis , : 1076 b) T. N. Balasubramaniam and N. R. Natale, Tetrahedron Lett., in press.
  • Natale , N. R. , Balasubramaniam , T. N. and Knerr , G. in press . J. Organomet. Chem. ,
  • Mirzaei , Y. R. , Simpson , B. M. , Triggle , D. J. and Natale , N. R. 1992 . J. Org. Chem. , 57 : 6271
  • De Amici , M. , De Micheli , C. , Carrea , G. and Spezia , S. 1989 . J. Org. Chem. , 54 : 2646 For a report of the preparation of chiral isoxazole derivatives using enzymatic methods, see: b) G. Binachi, G. Comi and I. Venturini, Gazz. Chem. Ital., 114, 285(1984); c) the diastereoselectivity of the addition of 4-metallo-isoxazoles to α,α'-disubstituted cycloalkanones has been described: C. Polo, V. Ramos, T. Torroba, M. L. Rodriguez, R. Bossio, S. Maracaccini and R. Pepino, Heterocycles, 32, 1757(1991).
  • Lutomski , K. A. and Meyers , A. I. 1984 . Asymmetric Synthesis , Edited by: Morrison , J. D. Vol. 3 , 213 – 274 . New York, NY : Academic Press .
  • Evans , D. A. 1984 . Asymmetric Synthesis , Edited by: Morrison , J. D. Vol. 3 , 1 – 110 . New York, NY : Academic Press .
  • Schlessinger , R. H. , Doss , M. A. and Richardson , S. 1986 . J. Am. Chem. Soc. , 108 : 3112
  • Bauer , W. and Seebach , D. 1984 . Helv. Chim. Acta , 67 : 1972

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.