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Volumn 62, Issue 16, 2006, Pages 3882-3895

Synthesis of 3-(arylmethylene)isoindolin-1-ones from ynamides by Heck-Suzuki-Miyaura domino reactions. Application to the synthesis of lennoxamine

Author keywords

Isoindolinones; Lennoxomine; Suzuki Miyaura reactions; Ynamides

Indexed keywords

2,3 DIMETHOXYBENZOIC ACID; 3 ARYLMETHYLENE ISOINDOLIN 1 ONE DERIVATIVE; AMIDE; AMINE; BENZAZEPINE DERIVATIVE; BENZOIC ACID; BORONIC ACID DERIVATIVE; ISOINDOLE DERIVATIVE; ISOINDOLOBENZAZEPINE ALKALOID; LENNOXAMINE; PALLADIUM; UNCLASSIFIED DRUG; YNAMIDE DERIVATIVE;

EID: 33645297163     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.11.089     Document Type: Article
Times cited : (120)

References (112)
  • 1
    • 0002981204 scopus 로고
    • Brossi, A., Ed. Academic: New York
    • Chang, Z.-L.; Zhu, D. Y. In The Alkaloids: Brossi, A., Ed. Academic: New York, 1978; vol. 31, pp 29-65.
    • (1978) The Alkaloids , vol.31 , pp. 29-65
    • Chang, Z.-L.1    Zhu, D.Y.2
  • 5
    • 12344337726 scopus 로고
    • (Italy) Jpn. Patent 59046268, 1984
    • Laboratori Baldacci, S. p. A. (Italy) Jpn. Patent 59046268, 1984; Chem. Abstr. 1984, 101, 54922.
    • (1984) Chem. Abstr. , vol.101 , pp. 54922
  • 7
    • 0030597152 scopus 로고    scopus 로고
    • For the addition of organolithium or Grignard reagents, see: (a) Pigeon, P.; Decroix, B. Tetrahedron Lett. 1996, 37, 7707-7710.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7707-7710
    • Pigeon, P.1    Decroix, B.2
  • 14
    • 0035955852 scopus 로고    scopus 로고
    • Organosamarium reagents can be also used, see: (h) Li, Z.; Zhang, Y. Tetrahedron Lett. 2001, 42, 8507-8510.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 8507-8510
    • Li, Z.1    Zhang, Y.2
  • 27
    • 0034733535 scopus 로고    scopus 로고
    • and references therein
    • (c) Kundu, N. G.; Khan, M. W. Tetrahedron 2000, 56, 4777-4792 and references therein.
    • (2000) Tetrahedron , vol.56 , pp. 4777-4792
    • Kundu, N.G.1    Khan, M.W.2
  • 29
    • 0033550205 scopus 로고    scopus 로고
    • A related approach involves the anionic cylization of 2-alkynylbenzonitriles initiated by treatement with sodium methoxide, see: (e) Wu, M.-J.; Chang, L.-J.; Wei, L.-M.; Lin, C.-F. Tetrahedron 1999, 55, 13193-13200.
    • (1999) Tetrahedron , vol.55 , pp. 13193-13200
    • Wu, M.-J.1    Chang, L.-J.2    Wei, L.-M.3    Lin, C.-F.4
  • 31
    • 0030861494 scopus 로고    scopus 로고
    • Electrophilic cyclizations of 2-alkynylbenzamides have also been reported, see: (a) Kundu, N. G.; Khan, M. W. Tetrahedron Lett. 1997, 38, 6937-6940.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 6937-6940
    • Kundu, N.G.1    Khan, M.W.2
  • 48
    • 0042069896 scopus 로고    scopus 로고
    • and references therein
    • (c) For an account on the synthesis of ynamides, see: Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P. Synlett 2003, 1379-1390 and references therein.
    • (2003) Synlett , pp. 1379-1390
    • Mulder, J.A.1    Kurtz, K.C.M.2    Hsung, R.P.3
  • 80
  • 83
    • 84993869046 scopus 로고
    • and references therein
    • (d) Grigg, R. J. Heterocycl. Chem. 1994, 31, 631-639 and references therein.
    • (1994) J. Heterocycl. Chem. , vol.31 , pp. 631-639
    • Grigg, R.1
  • 111
    • 2342596963 scopus 로고    scopus 로고
    • A copper-catalyzed coupling between alkynyl bromides and amides constitutes an efficient access to ynamides, see: Zhang, Y.; Hsung, R. P.; Tracey, M. R.; Kurtz, K. C. M.; Vera, E. L. Org. Lett. 2004, 6, 1151-1154. Such coupling between phenylethynyl bromide and amide 29 as substrate turned out to be unsuccessful.
    • (2004) Org. Lett. , vol.6 , pp. 1151-1154
    • Zhang, Y.1    Hsung, R.P.2    Tracey, M.R.3    Kurtz, K.C.M.4    Vera, E.L.5
  • 112
    • 0000344537 scopus 로고
    • 2, 0°C) and subsequent treatment of the dibromoolefin with n-BuLi (2 equiv), THF, K78°C (73% overall yield), see: Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769-3772.
    • (1972) Tetrahedron Lett. , pp. 3769-3772
    • Corey, E.J.1    Fuchs, P.L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.