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Volumn , Issue 4, 1998, Pages 399-401

New and convenient synthesis of pyrrolo[1,2-a]benzimidazoles and indolizinones based on regioselective cyclization reactions of heterocyclic dianions

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EID: 0001250164     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1673     Document Type: Article
Times cited : (24)

References (37)
  • 2
    • 26844496022 scopus 로고    scopus 로고
    • For part 2 see Synlett, 1998, 396.
    • (1998) Synlett , Issue.2 PART , pp. 396
  • 3
  • 4
    • 0025865630 scopus 로고
    • For a review on the application of dianions in organic syntheses, see: Thompson, C. M.; Green, D. Tetrahedron 1991, 47, 4223.
    • (1991) Tetrahedron , vol.47 , pp. 4223
    • Thompson, C.M.1    Green, D.2
  • 16
    • 0002445053 scopus 로고    scopus 로고
    • For cyclization reactions of 1,1-dianions, see: Langer, P.; Döring, M.; Synlett 1998, 396.
    • (1998) Synlett , pp. 396
    • Langer, P.1    Döring, M.2
  • 21
    • 84918118119 scopus 로고
    • Oxa-analogous 1H-pyrrolo[1,2-a]benzimidazole-1-ones have been previously prepared by a different approach: Ried, W.; Knorr, H. Liebigs Ann. Chem. 1976, 284.
    • (1976) Liebigs Ann. Chem. , pp. 284
    • Ried, W.1    Knorr, H.2
  • 22
    • 26844471659 scopus 로고    scopus 로고
    • note
    • 5: C. 79.64; H, 5.39; N, 14.97. Found: C, 79.84; H, 5.95; N, 15.50. For all dianion cyclizations reported herein, virtually no heterocyclic side products were formed. Some ether insoluble polymeric material was formed from which the product was separated by flash-chromatography. In some cases small amounts of ArNC (< 10 % yield) were isolated, which derive from reductive cleavage of the carbon-carbon bond of 2a,b.
  • 24
    • 0001133088 scopus 로고
    • For reviews on radialenes, see: Hopf, H.; Maas, G. Angew. Chem. 1992, 104, 953-977;
    • (1992) Angew. Chem. , vol.104 , pp. 953-977
    • Hopf, H.1    Maas, G.2
  • 27
    • 26844472746 scopus 로고    scopus 로고
    • note
    • HMO Calculations suggest that the activated complex deriving from tautomer B is more stable than the complex deriving from tautomer A (using ethylene as dienophile).
  • 29
    • 0000286244 scopus 로고
    • (b) An oxa-analogue of this heterocyclic system has been previously prepared: Walker, G. N.; Weaver, B. N. J. Org. Chem. 1961, 26, 4441.
    • (1961) J. Org. Chem. , vol.26 , pp. 4441
    • Walker, G.N.1    Weaver, B.N.2
  • 30
    • 84985554204 scopus 로고
    • Push-pull substituted cyclic π-systems are of theoretical interest and of importance in the field of material sciences: For an excellent review see: (a) Gompper, R.; Wagner, H.-U. Angew. Chem., Int. Ed. Engl. 1988, 27, 1437.
    • (1988) Angew. Chem., Int. Ed. Engl. , vol.27 , pp. 1437
    • Gompper, R.1    Wagner, H.-U.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.