메뉴 건너뛰기




Volumn 346, Issue 13-15, 2004, Pages 1661-1664

A domino copper-catalyzed C-N and C-O cross-coupling for the conversion of primary amides into benzoxazoles

Author keywords

Benzoxazoles; C N and C O cross coupling; Copper; Cyclization; Domino reactions; Heterocycles

Indexed keywords

AMIDE; BENZOXAZOLE DERIVATIVE; COPPER;

EID: 12344278958     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404182     Document Type: Article
Times cited : (187)

References (58)
  • 14
    • 84943373693 scopus 로고
    • (Eds.: A. R. Katritzky, C. W. Rees, K. T. Potts), Pergamon Press, New York
    • c) G. V. Boyd, in: Comprehensive Heterocyclic Chemistry, Vol. 6 (Eds.: A. R. Katritzky, C. W. Rees, K. T. Potts), Pergamon Press, New York, 1984, pp. 177-223;
    • (1984) Comprehensive Heterocyclic Chemistry , vol.6 , pp. 177-223
    • Boyd, G.V.1
  • 22
    • 12344261272 scopus 로고    scopus 로고
    • [5a] pp 1089-1091
    • [5a] pp 1089-1091;
  • 30
    • 0027171310 scopus 로고
    • For the cyclization of 2-halo-3-amidopyridines, see: a) M. H. Norman, D. J. Douglas, G. E. Martin, J. Heterocycl. Chem. 1993, 30, 771-780; b) C. Flouzant, G. Guillaumet, Synthesis 1990, 64-66; c) C. Flouzat, G. Guillaumet, J. Heterocycl. Chem. 1991, 28, 899-906; d) P. Savarino, G. Viscardi, R. Carpignano, E. Barni, J. Heterocycl. Chem. 1989, 26, 77-80; for a Cu-mediated process, see: e) J.-F. Briere, G. Dupas, G. Queguiner, J. Bourguignon, Heterocycles 2000, 52, 1371-1384.
    • (1993) J. Heterocycl. Chem. , vol.30 , pp. 771-780
    • Norman, M.H.1    Douglas, D.J.2    Martin, G.E.3
  • 31
    • 84986460501 scopus 로고
    • For the cyclization of 2-halo-3-amidopyridines, see: a) M. H. Norman, D. J. Douglas, G. E. Martin, J. Heterocycl. Chem. 1993, 30, 771-780; b) C. Flouzant, G. Guillaumet, Synthesis 1990, 64-66; c) C. Flouzat, G. Guillaumet, J. Heterocycl. Chem. 1991, 28, 899-906; d) P. Savarino, G. Viscardi, R. Carpignano, E. Barni, J. Heterocycl. Chem. 1989, 26, 77-80; for a Cu-mediated process, see: e) J.-F. Briere, G. Dupas, G. Queguiner, J. Bourguignon, Heterocycles 2000, 52, 1371-1384.
    • (1990) Synthesis , pp. 64-66
    • Flouzant, C.1    Guillaumet, G.2
  • 32
    • 84986462319 scopus 로고
    • For the cyclization of 2-halo-3-amidopyridines, see: a) M. H. Norman, D. J. Douglas, G. E. Martin, J. Heterocycl. Chem. 1993, 30, 771-780; b) C. Flouzant, G. Guillaumet, Synthesis 1990, 64-66; c) C. Flouzat, G. Guillaumet, J. Heterocycl. Chem. 1991, 28, 899-906; d) P. Savarino, G. Viscardi, R. Carpignano, E. Barni, J. Heterocycl. Chem. 1989, 26, 77-80; for a Cu-mediated process, see: e) J.-F. Briere, G. Dupas, G. Queguiner, J. Bourguignon, Heterocycles 2000, 52, 1371-1384.
    • (1991) J. Heterocycl. Chem. , vol.28 , pp. 899-906
    • Flouzat, C.1    Guillaumet, G.2
  • 33
    • 84986519283 scopus 로고
    • For the cyclization of 2-halo-3-amidopyridines, see: a) M. H. Norman, D. J. Douglas, G. E. Martin, J. Heterocycl. Chem. 1993, 30, 771-780; b) C. Flouzant, G. Guillaumet, Synthesis 1990, 64-66; c) C. Flouzat, G. Guillaumet, J. Heterocycl. Chem. 1991, 28, 899-906; d) P. Savarino, G. Viscardi, R. Carpignano, E. Barni, J. Heterocycl. Chem. 1989, 26, 77-80; for a Cu-mediated process, see: e) J.-F. Briere, G. Dupas, G. Queguiner, J. Bourguignon, Heterocycles 2000, 52, 1371-1384.
    • (1989) J. Heterocycl. Chem. , vol.26 , pp. 77-80
    • Savarino, P.1    Viscardi, G.2    Carpignano, R.3    Barni, E.4
  • 34
    • 0034163724 scopus 로고    scopus 로고
    • For the cyclization of 2-halo-3-amidopyridines, see: a) M. H. Norman, D. J. Douglas, G. E. Martin, J. Heterocycl. Chem. 1993, 30, 771-780; b) C. Flouzant, G. Guillaumet, Synthesis 1990, 64-66; c) C. Flouzat, G. Guillaumet, J. Heterocycl. Chem. 1991, 28, 899-906; d) P. Savarino, G. Viscardi, R. Carpignano, E. Barni, J. Heterocycl. Chem. 1989, 26, 77-80; for a Cu-mediated process, see: e) J.-F. Briere, G. Dupas, G. Queguiner, J. Bourguignon, Heterocycles 2000, 52, 1371-1384.
    • (2000) Heterocycles , vol.52 , pp. 1371-1384
    • Briere, J.-F.1    Dupas, G.2    Queguiner, G.3    Bourguignon, J.4
  • 36
    • 12344257386 scopus 로고
    • (Hodogaya Chemical Co., Ltd.), US Patent 3147253, 1964
    • b) M. Iizuka, M. Yamamoto, J. Matsumura, M. Yoshida (Hodogaya Chemical Co., Ltd.), US Patent 3147253, 1964; Chem. Abstr. 1964, 67, 16209.
    • (1964) Chem. Abstr. , vol.67 , pp. 16209
    • Iizuka, M.1    Yamamoto, M.2    Matsumura, J.3    Yoshida, M.4
  • 41
    • 1442300776 scopus 로고    scopus 로고
    • For some related transition-metal catalyzed cyclizations, see: a) L. L. Joyce, G. Evindar, R. A. Batey, Chem. Commun. 2004, 446-447; b) G. Evindar, R. A. Batey, Org, Lett. 2003, 5, 133-136; c) C. Benedi, F. Bravo, P. Uriz, E. Fernandez, C. Claver, S. Castillon, Tetrahedron Lett. 2003, 44, 6073-6077; d) C. T. Brain, J. T. Steer, J. Org. Chem. 2003, 68, 6814-6816 and references cited therein.
    • (2004) Chem. Commun. , pp. 446-447
    • Joyce, L.L.1    Evindar, G.2    Batey, R.A.3
  • 42
    • 0038003832 scopus 로고    scopus 로고
    • For some related transition-metal catalyzed cyclizations, see: a) L. L. Joyce, G. Evindar, R. A. Batey, Chem. Commun. 2004, 446-447; b) G. Evindar, R. A. Batey, Org, Lett. 2003, 5, 133-136; c) C. Benedi, F. Bravo, P. Uriz, E. Fernandez, C. Claver, S. Castillon, Tetrahedron Lett. 2003, 44, 6073-6077; d) C. T. Brain, J. T. Steer, J. Org. Chem. 2003, 68, 6814-6816 and references cited therein.
    • (2003) Org, Lett. , vol.5 , pp. 133-136
    • Evindar, G.1    Batey, R.A.2
  • 43
    • 0038644140 scopus 로고    scopus 로고
    • For some related transition-metal catalyzed cyclizations, see: a) L. L. Joyce, G. Evindar, R. A. Batey, Chem. Commun. 2004, 446-447; b) G. Evindar, R. A. Batey, Org, Lett. 2003, 5, 133-136; c) C. Benedi, F. Bravo, P. Uriz, E. Fernandez, C. Claver, S. Castillon, Tetrahedron Lett. 2003, 44, 6073-6077; d) C. T. Brain, J. T. Steer, J. Org. Chem. 2003, 68, 6814-6816 and references cited therein.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 6073-6077
    • Benedi, C.1    Bravo, F.2    Uriz, P.3    Fernandez, E.4    Claver, C.5    Castillon, S.6
  • 44
    • 0043009828 scopus 로고    scopus 로고
    • and references cited therein
    • For some related transition-metal catalyzed cyclizations, see: a) L. L. Joyce, G. Evindar, R. A. Batey, Chem. Commun. 2004, 446-447; b) G. Evindar, R. A. Batey, Org, Lett. 2003, 5, 133-136; c) C. Benedi, F. Bravo, P. Uriz, E. Fernandez, C. Claver, S. Castillon, Tetrahedron Lett. 2003, 44, 6073-6077; d) C. T. Brain, J. T. Steer, J. Org. Chem. 2003, 68, 6814-6816 and references cited therein.
    • (2003) J. Org. Chem. , vol.68 , pp. 6814-6816
    • Brain, C.T.1    Steer, J.T.2
  • 45
  • 46
    • 12344324351 scopus 로고    scopus 로고
    • note
    • [12c]
  • 47
    • 0345708168 scopus 로고    scopus 로고
    • Profound reviews on Cu-catalyzed C-N, C-O and C-S couplings: a) S. V. Ley, A. W. Thomas, Angew. Chem. Int. Ed. 2003, 42, 5400-5449; b) K. Kunz, U. Scholz, D. Ganzer, Synlett 2003, 2428-2439.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 5400-5449
    • Ley, S.V.1    Thomas, A.W.2
  • 48
    • 0346749657 scopus 로고    scopus 로고
    • Profound reviews on Cu-catalyzed C-N, C-O and C-S couplings: a) S. V. Ley, A. W. Thomas, Angew. Chem. Int. Ed. 2003, 42, 5400-5449; b) K. Kunz, U. Scholz, D. Ganzer, Synlett 2003, 2428-2439.
    • (2003) Synlett , pp. 2428-2439
    • Kunz, K.1    Scholz, U.2    Ganzer, D.3
  • 50
    • 12344271675 scopus 로고    scopus 로고
    • note
    • 3 as a base resulted in comparable results.
  • 55
    • 12344321173 scopus 로고    scopus 로고
    • [16]
    • [16]
  • 56
    • 12344252435 scopus 로고    scopus 로고
    • note
    • 6; ligands: 1,2-diaminocyclohexane, N,N′-dimethylethylenediamine, phenanthroline, proline.
  • 57
    • 12344284448 scopus 로고    scopus 로고
    • note
    • Whereas the regiochemistry of the 4e, 4f and 4h was firmly established, the regiochemistry of 4g was assigned by analogy only.
  • 58
    • 0141561377 scopus 로고
    • However, the uncatalyzed coupling and cyclization of activated hexafluorobenzene and benzamide in 32% yield has been reported as a one-step procedure: Y. Inukai, T. Sonoda, H. Kobayashi, Bull. Chem. Soc. Jpn. 1979, 52, 2657-2660.
    • (1979) Bull. Chem. Soc. Jpn. , vol.52 , pp. 2657-2660
    • Inukai, Y.1    Sonoda, T.2    Kobayashi, H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.