메뉴 건너뛰기




Volumn 50, Issue 18, 2009, Pages 2129-2131

Divergent synthesis of isoindolo[2,1-a]indole and indolo[1,2-a]indole through copper-catalysed C- and N-arylations

Author keywords

Arylation; Copper catalysts; Indoles

Indexed keywords

CARBON; COPPER; INDOLE DERIVATIVE; INDOLO[1,2 A]INDOLE; ISOINDOLO[2,1 A]INDOLE; NITROGEN; UNCLASSIFIED DRUG;

EID: 62649157221     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.175     Document Type: Article
Times cited : (37)

References (47)
  • 1
    • 0034006916 scopus 로고    scopus 로고
    • A review of indole-containing natural products:
    • A review of indole-containing natural products:. Lounasmaa M., and Tolvanen A. Nat. Prod. Rep. 17 (2000) 175-191
    • (2000) Nat. Prod. Rep. , vol.17 , pp. 175-191
    • Lounasmaa, M.1    Tolvanen, A.2
  • 2
    • 62649098650 scopus 로고
    • Vinblastine and Vincristine alkaloids belong to Vinca family and they have been widely used in medicine for treating diverse types of cancer (lymphomas, sarcomas, testicular and breast cancer, leukaemia, etc.) due to their strong antineoplastic activity. See: Antitumor Bisindole Alkaloids from Catharanthus roseus (L.). Brossi A., and Suffness M. (Eds), Academic Press, New York and references cited therein
    • Vinblastine and Vincristine alkaloids belong to Vinca family and they have been widely used in medicine for treating diverse types of cancer (lymphomas, sarcomas, testicular and breast cancer, leukaemia, etc.) due to their strong antineoplastic activity. See: Antitumor Bisindole Alkaloids from Catharanthus roseus (L.). In: Brossi A., and Suffness M. (Eds). The Alkaloids Vol. 37 (1990), Academic Press, New York 1-240 and references cited therein
    • (1990) The Alkaloids , vol.37 , pp. 1-240
  • 5
    • 34547274208 scopus 로고    scopus 로고
    • Only a few spattered examples of isolated indolo[1,2-a]indoles have been reported thus far, and mostly as byproducts or in low yields. See:
    • Only a few spattered examples of isolated indolo[1,2-a]indoles have been reported thus far, and mostly as byproducts or in low yields. See:. Samsoniya Sh.A., and Trapaidze M.V. Russ. Chem. Rev. 76 (2007) 313-326
    • (2007) Russ. Chem. Rev. , vol.76 , pp. 313-326
    • Samsoniya, Sh.A.1    Trapaidze, M.V.2
  • 14
    • 0010372638 scopus 로고
    • The intramolecular direct arylation of indole with aryl iodides through a palladium-catalysed process was first reported by Grigg and co-workers. See:
    • The intramolecular direct arylation of indole with aryl iodides through a palladium-catalysed process was first reported by Grigg and co-workers. See:. Grigg R., Sridharan V., Stevenson P., Sukirthalingam S., and Worakun T. Tetrahedron 46 (1990) 4003-4018
    • (1990) Tetrahedron , vol.46 , pp. 4003-4018
    • Grigg, R.1    Sridharan, V.2    Stevenson, P.3    Sukirthalingam, S.4    Worakun, T.5
  • 15
    • 31544455027 scopus 로고    scopus 로고
    • Recently, Fagnou et al. published the preparation of isoindolo[2,1-a]indole 1 through an intramolecular palladium-catalysed direct arylation of an aryl chloride. See:
    • Recently, Fagnou et al. published the preparation of isoindolo[2,1-a]indole 1 through an intramolecular palladium-catalysed direct arylation of an aryl chloride. See:. Campeau L.-C., Parisien M., Jean A., Fagnou K. J. Am. Chem. Soc. 128 (2006) 581-590
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 581-590
    • Campeau, L.-C.1    Parisien, M.2    Jean, A.3    Fagnou, K.4
  • 17
    • 18844405201 scopus 로고    scopus 로고
    • A palladium-catalysed indole alkenylation by C-H functionalisation aided by copper oxidants is reported in:
    • A palladium-catalysed indole alkenylation by C-H functionalisation aided by copper oxidants is reported in:. Grimser N.P., Gaunlett C., Godfrey C.R.A., and Gaunt M.J. Angew. Chem., Int. Ed. 44 (2005) 3125-3129
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 3125-3129
    • Grimser, N.P.1    Gaunlett, C.2    Godfrey, C.R.A.3    Gaunt, M.J.4
  • 21
    • 42949170450 scopus 로고    scopus 로고
    • Recently, an iron-catalysed direct arylation of α-benzoquinolines has been reported. See:
    • Recently, an iron-catalysed direct arylation of α-benzoquinolines has been reported. See:. Norinder J., Matsumoto A., Yoshikai N., and Nakamura E. J. Am. Chem. Soc. 130 (2008) 5858-5859
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 5858-5859
    • Norinder, J.1    Matsumoto, A.2    Yoshikai, N.3    Nakamura, E.4
  • 22
    • 2442685496 scopus 로고    scopus 로고
    • He et al. reported a gold-catalysed functionalisation of aromatic C-H bonds. See:
    • He et al. reported a gold-catalysed functionalisation of aromatic C-H bonds. See:. Shi Z., He C. J. Org. Chem. 69 (2004) 3669-3671
    • (2004) J. Org. Chem. , vol.69 , pp. 3669-3671
    • Shi, Z.1    He, C.2
  • 25
    • 47749142816 scopus 로고    scopus 로고
    • For a review on catalytic C-C, C-N and C-O Ullmann-type coupling reactions, see:
    • For a review on catalytic C-C, C-N and C-O Ullmann-type coupling reactions, see:. Monnier F., and Taillefer M. Angew. Chem., Int. Ed. 47 (2008) 3096-3099
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 3096-3099
    • Monnier, F.1    Taillefer, M.2
  • 29
    • 54049087464 scopus 로고    scopus 로고
    • 2 (1.0 equiv) has been used for non-selective, multiple C-H bond arylation of indoles and pyrroles. See:
    • 2 (1.0 equiv) has been used for non-selective, multiple C-H bond arylation of indoles and pyrroles. See:. Ban I., Sudo T., Taniguchi T., and Itami K. Org. Lett. 10 (2008) 3607-3609
    • (2008) Org. Lett. , vol.10 , pp. 3607-3609
    • Ban, I.1    Sudo, T.2    Taniguchi, T.3    Itami, K.4
  • 30
    • 53049104239 scopus 로고    scopus 로고
    • and references cited therein
    • Borduas N., and Powell D.A. J. Org. Chem. 73 (2008) 7822-7825 and references cited therein
    • (2008) J. Org. Chem. , vol.73 , pp. 7822-7825
    • Borduas, N.1    Powell, D.A.2
  • 34
    • 4143104684 scopus 로고    scopus 로고
    • Only N-arylation of unprotected indoles has been achieved thus far, as reported by Buchwald. See:
    • Only N-arylation of unprotected indoles has been achieved thus far, as reported by Buchwald. See:. Antilla J.C., Baskin J.M., Barder T.E., and Buchwald S.L. J. Org. Chem. 69 (2004) 5578-5587
    • (2004) J. Org. Chem. , vol.69 , pp. 5578-5587
    • Antilla, J.C.1    Baskin, J.M.2    Barder, T.E.3    Buchwald, S.L.4
  • 35
    • 46049110936 scopus 로고    scopus 로고
    • A direct, elegant arylation of indoles using diaryl-iodine(III) reagents can be found in:
    • A direct, elegant arylation of indoles using diaryl-iodine(III) reagents can be found in:. Phipps R.J., Grimster N.P., and Gaunt M.J. J. Am. Chem. Soc. 130 (2008) 8172-8174
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 8172-8174
    • Phipps, R.J.1    Grimster, N.P.2    Gaunt, M.J.3
  • 38
    • 40849119590 scopus 로고    scopus 로고
    • The use of PEG as additive and/or solvent in copper-catalysed reactions has been reported. See:
    • The use of PEG as additive and/or solvent in copper-catalysed reactions has been reported. See:. Mao J., Guo J., Fang F., and Ji S.-J. Tetrahedron 64 (2008) 3905-3911
    • (2008) Tetrahedron , vol.64 , pp. 3905-3911
    • Mao, J.1    Guo, J.2    Fang, F.3    Ji, S.-J.4
  • 44
    • 33645910529 scopus 로고    scopus 로고
    • Apparently, the aliphatic diamine could play both the role of base and ligand. See:
    • Apparently, the aliphatic diamine could play both the role of base and ligand. See:. Carril M., SanMartin R., Tellitu M., and Domínguez E. Org. Lett. 8 (2006) 1467-1470
    • (2006) Org. Lett. , vol.8 , pp. 1467-1470
    • Carril, M.1    SanMartin, R.2    Tellitu, M.3    Domínguez, E.4
  • 45
    • 0034794463 scopus 로고    scopus 로고
    • These conditions had proved successful for the N-arylation of some nitrogen-containing heterocycles. See:
    • These conditions had proved successful for the N-arylation of some nitrogen-containing heterocycles. See:. Klapars A., Antilla J.C., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 123 (2001) 7727-7729
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 7727-7729
    • Klapars, A.1    Antilla, J.C.2    Huang, X.3    Buchwald, S.L.4
  • 46
    • 62649093409 scopus 로고    scopus 로고
    • note
    • 4 and concentrated in vacuo. The resulting residue was purified by flash chromatography (10% AcOEt/n-hexane) to afford the target tetracyclic product 1 as a white powder (52.3 mg, 88%). The physical data were compared with those found in the literature. See: Ref. 9c.
  • 47
    • 62649107779 scopus 로고    scopus 로고
    • note
    • 4 and concentrated in vacuo. The resulting residue was purified by flash chromatography (10% AcOEt/n-hexane) to afford the target tetracyclic product 2 as a white powder (51.0 mg, 88%). For physical data see Supplementary data.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.