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Volumn 70, Issue 6, 2005, Pages 2054-2059

Selective partial reduction of various heteroaromatic compounds with bridgehead nitrogen via birch reduction protocol

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CATALYST ACTIVITY; CHEMICAL BONDS; HYDROGENATION; NITROGEN; OLEFINS; REDUCTION;

EID: 15444368644     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0479157     Document Type: Article
Times cited : (40)

References (29)
  • 7
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    • CA 115:183038
    • For attempts on selective partial reduction of pyrroloheterocycles using catalytic hydrogenation, see: (a) Khorkhe, R. A.; Sodatova, S. A.; Sodatenkov, A. T.; Ryashentseva, M. A.; Prostakov, N. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1991. 6, 1413; CA 115:183038. (b) Alarcon, H. A. R.; Soldatenkov, A. T.; Soldatova, S. A.; Samalyoa, A. I.; Obando, H. U.; Prostakov, N. S. Khim. Geterotsikl. Soedin. 1993, 9, 1233; CA 120:270057.
    • (1991) Izv. Akad. Nauk SSSR, Ser. Khim. , vol.6 , pp. 1413
    • Khorkhe, R.A.1    Sodatova, S.A.2    Sodatenkov, A.T.3    Ryashentseva, M.A.4    Prostakov, N.S.5
  • 8
    • 25444506567 scopus 로고
    • CA 120:270057
    • For attempts on selective partial reduction of pyrroloheterocycles using catalytic hydrogenation, see: (a) Khorkhe, R. A.; Sodatova, S. A.; Sodatenkov, A. T.; Ryashentseva, M. A.; Prostakov, N. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1991. 6, 1413; CA 115:183038. (b) Alarcon, H. A. R.; Soldatenkov, A. T.; Soldatova, S. A.; Samalyoa, A. I.; Obando, H. U.; Prostakov, N. S. Khim. Geterotsikl. Soedin. 1993, 9, 1233; CA 120:270057.
    • (1993) Khim. Geterotsikl. Soedin. , vol.9 , pp. 1233
    • Alarcon, H.A.R.1    Soldatenkov, A.T.2    Soldatova, S.A.3    Samalyoa, A.I.4    Obando, H.U.5    Prostakov, N.S.6
  • 13
    • 77957047508 scopus 로고    scopus 로고
    • Studies in Natural Products Chemistry
    • Bowden, B. F. Studies in Natural Products Chemistry. In Bioact. Nat. Prod. (Part D) 2000, 23, 233.
    • (2000) Bioact. Nat. Prod. (Part D) , vol.23 , pp. 233
    • Bowden, B.F.1
  • 18
    • 15444381098 scopus 로고    scopus 로고
    • note
    • 73% yield of 5 was due to the highly acid-sensitive nature of 5.
  • 19
    • 0021173291 scopus 로고
    • For the installation of a quaternary carbon center in the Birch reduction, see for examples: (a) Schultz, A. G.; Sundararaman, P. Tetrahedron Lett. 1984, 25, 4591. (b) Donohoe, T. J.; Guyo, P. M. J. Org. Chem. 1996, 61, 7664.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 4591
    • Schultz, A.G.1    Sundararaman, P.2
  • 20
    • 0001570826 scopus 로고    scopus 로고
    • For the installation of a quaternary carbon center in the Birch reduction, see for examples: (a) Schultz, A. G.; Sundararaman, P. Tetrahedron Lett. 1984, 25, 4591. (b) Donohoe, T. J.; Guyo, P. M. J. Org. Chem. 1996, 61, 7664.
    • (1996) J. Org. Chem. , vol.61 , pp. 7664
    • Donohoe, T.J.1    Guyo, P.M.2
  • 23
    • 15444368063 scopus 로고    scopus 로고
    • For the suppression of Birch over-reduction by converting benzoic acid to a carboxylate salt, see: Mander, L. N.; Morris, J. C. J. Org. Chem. 1997, 62, 7497.
    • (1997) J. Org. Chem. , vol.62 , pp. 7497
    • Mander, L.N.1    Morris, J.C.2
  • 24
    • 15444368482 scopus 로고    scopus 로고
    • note
    • Introduction of alkoxide had dramatically increased the energy of LUMO (3.55 eV in 22 vs -0.17 eV and -0.48 eV for 17 and 19, respectively), which resulted in significantly slower reduction (6 h for 22 vs 10-20 min for 17 and 19).
  • 25
    • 15444373166 scopus 로고    scopus 로고
    • note
    • For complications in Birch reduction in the presense of an internal proton source, see ref 14.
  • 27
    • 15444377279 scopus 로고    scopus 로고
    • note
    • The relative configuration of 32 was confirmed by a NOESY experiment. NOE was observed between the hydrogen at C-4 and the methyl group at C-5 (so it was between the methyl group at the C-4 position and the hydrogen at the C-5 position).


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