메뉴 건너뛰기




Volumn , Issue 11, 1999, Pages 2997-3003

Iodocyclisation of 1,4-dihydropyridines; synthesis and reactivity of 1- iodoindolo[2,3-a]quinolizidines

Author keywords

Alkaloids; Cyclizations; Iodine; Nitrogen heterocycles; Oxidations

Indexed keywords

1,4 DIHYDROPYRIDINE DERIVATIVE; AMPHOLYTE; INDOLE DERIVATIVE; IODINE; QUINOLINE DERIVATIVE;

EID: 0032726765     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199911)1999:11<2997::aid-ejoc2997>3.0.co;2-%23     Document Type: Article
Times cited : (22)

References (52)
  • 10
    • 0000390061 scopus 로고
    • S. Goldmann, J. Stoltefuss, Angew. Chem. 1991, 103, 1587-1606; Angew. Chem. Int. Ed. Engl. 1991, 30, 1559-1578.
    • (1991) Angew. Chem. , vol.103 , pp. 1587-1606
    • Goldmann, S.1    Stoltefuss, J.2
  • 11
    • 0026342780 scopus 로고
    • S. Goldmann, J. Stoltefuss, Angew. Chem. 1991, 103, 1587-1606; Angew. Chem. Int. Ed. Engl. 1991, 30, 1559-1578.
    • (1991) Angew. Chem. Int. Ed. Engl. , vol.30 , pp. 1559-1578
  • 18
    • 0000772498 scopus 로고    scopus 로고
    • Special care should be taken with hydroxy-substituted dihydropyridines 1a-c because of their propensity to undergo acid-catalysed cyclisation yielding the corresponding oxazolidines or oxazines. It is therefore advisable to use them immediately after preparation. For an account of this transformation with synthetic applications see: Y.-S. Wong, C. Marazano, D. Gnecco, Y. Génisson, A. Chiaroni, B.C. Das, J. Org. Chem. 1997, 62, 729-733.
    • (1997) J. Org. Chem. , vol.62 , pp. 729-733
    • Wong, Y.-S.1    Marazano, C.2    Gnecco, D.3    Génisson, Y.4    Chiaroni, A.5    Das, B.C.6
  • 20
    • 0010426184 scopus 로고
    • For representative examples, see: [18a] R. Amann, D. Spitzner, Angew. Chem. 1991, 103, 1373-1374; Angew. Chem. Int. Ed. Engl. 1991, 30, 1320-1321.
    • (1991) Angew. Chem. , vol.103 , pp. 1373-1374
    • Amann, R.1    Spitzner, D.2
  • 21
    • 0026051825 scopus 로고
    • For representative examples, see: [18a] R. Amann, D. Spitzner, Angew. Chem. 1991, 103, 1373-1374; Angew. Chem. Int. Ed. Engl. 1991, 30, 1320-1321.
    • (1991) Angew. Chem. Int. Ed. Engl. , vol.30 , pp. 1320-1321
  • 29
    • 0001046290 scopus 로고
    • In phenylglycinol-derived oxazolopiperidines, the chemical shift of the hemiaminal proton in the NMR spectrum appears at lower field in the isomers which bear the phenyl group at the same face. For instance, see: J. Royer, H.-P. Husson, Heterocycles 1993, 36, 1493-1496.
    • (1993) Heterocycles , vol.36 , pp. 1493-1496
    • Royer, J.1    Husson, H.-P.2
  • 30
    • 0003417469 scopus 로고
    • Ed.: B. M. Trost, Pergamon Press, Oxford, chapter 4.4
    • Although the indolizidine formation formally is a disfavoured process (5-endo-trig), several examples of this cyclisation are reported in the literature. For an excellent review see: L. E. Overman, D. J. Ricca in Comprehensive Organic Synthesis (Ed.: B. M. Trost), Pergamon Press, Oxford, 1991, vol. 2, chapter 4.4.
    • (1991) Comprehensive Organic Synthesis , vol.2
    • Overman, L.E.1    Ricca, D.J.2
  • 31
    • 85197329847 scopus 로고    scopus 로고
    • note
    • In MeOH solution no cyclisation took place, and the 3-iodo-2-methoxytetrahydropyridine was produced instead.
  • 39
    • 0345217830 scopus 로고
    • Ed.: L. A. Paquette, Wiley, Chichester
    • Although reduction of the organic halide is an undesired side process on Zn-mediated conjugate additions (see for instance ref [18d]) the method has wide applicability: P. Knochel in Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, Chichester, 1995, vol. 8, p.5526.
    • (1995) Encyclopedia of Reagents for Organic Synthesis , vol.8 , pp. 5526
    • Knochel, P.1
  • 41
    • 0042789931 scopus 로고
    • [30a] For a review on the radical-mediated ring-expansions (and ring-contractions), see: P. Dowd, W. Zhang, Chem. Rev. 1993, 93, 2091-2115.
    • (1993) Chem. Rev. , vol.93 , pp. 2091-2115
    • Dowd, P.1    Zhang, W.2
  • 42
    • 85197323650 scopus 로고    scopus 로고
    • note
    • [30b] The corresponding reduced cyclopropane analogue was not detected, which reflects the eagerness of cyclopropylcarbinyl radicals to undergo ring opening; for recent results in the field see:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.