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Volumn 47, Issue 26, 2008, Pages 4851-4854

Palladium(0)-catalyzed alkynyl and allenyl iminium ion cyclizations leading to 1,4-disubstituted 1,2,3,6-tetrahydropyridines

Author keywords

Heterocycles; Iminium ions; Multicomponent reactions; Organoboron reagents; Palladium

Indexed keywords

CHEMICAL COMPOUNDS; CHEMICAL REACTIONS; CYCLIZATION; ORGANOMETALLICS; PALLADIUM;

EID: 48849091957     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800823     Document Type: Article
Times cited : (38)

References (40)
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    • for cross-coupling reactions between metalated piperidines and organic halides, see: e
    • for cross-coupling reactions between metalated piperidines and organic halides, see: e) J. S. Kiely, E. Laborde, L. E. Lesheski, R. A. Bucsh, J. Heterocycl. Chem. 1991, 28, 1581-1585;
    • (1991) J. Heterocycl. Chem , vol.28 , pp. 1581-1585
    • Kiely, J.S.1    Laborde, E.2    Lesheski, L.E.3    Bucsh, R.A.4
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    • For other synthetic routes to 1, see: a C. J. Schmidle, R. C. Mansfield, J. Am. Chem. Soc. 1956, 78, 425-428;
    • For other synthetic routes to 1, see: a) C. J. Schmidle, R. C. Mansfield, J. Am. Chem. Soc. 1956, 78, 425-428;
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    • Angew. Chem. Int. Ed. 1999, 38, 2214-2217;
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    • 0042745386 scopus 로고    scopus 로고
    • For reviews on the multicomponent synthesis of heterocycles, see: a
    • For reviews on the multicomponent synthesis of heterocycles, see: a) R. V. A. Orru, M. de Greef, Synthesis 2003, 1471-1499;
    • (2003) Synthesis , pp. 1471-1499
    • Orru, R.V.A.1    de Greef, M.2
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    • 0-catalyzed tetrahydropyridine syntheses based on the carbocyclization of a 3,4-pentadienylamine with an organic halide to form both a carbon-carbon bond at C5 and a C6-N1 bond. The products of the latter reactions are often contaminated by the corresponding 2-alkenyl azetidine and 2,3-dihydropyrrole as by-products: a F. P. J. T. Rutjes, K. C. M. F. Tjen, L. B. Wolf, W. F. J. Karstens, H. E. Schoemaker, Org. Lett. 1999, 1, 717-720;
    • 0-catalyzed tetrahydropyridine syntheses based on the carbocyclization of a 3,4-pentadienylamine with an organic halide to form both a carbon-carbon bond at C5 and a C6-N1 bond. The products of the latter reactions are often contaminated by the corresponding 2-alkenyl azetidine and 2,3-dihydropyrrole as by-products: a) F. P. J. T. Rutjes, K. C. M. F. Tjen, L. B. Wolf, W. F. J. Karstens, H. E. Schoemaker, Org. Lett. 1999, 1, 717-720;
  • 37
    • 53549083113 scopus 로고    scopus 로고
    • Awide variety of starting materials 9 and 10 can be prepared by two-component coupling reactions, that is, the nucleophilic substitution of the methanesulfonate of a 3-butyn-1-ol or 2,3-butadien-1-ol with a primary amine, or the reductive amination of an aldehyde with a primary 3-butynylamine or 2,3-butadienylamine.
    • Awide variety of starting materials 9 and 10 can be prepared by two-component coupling reactions, that is, the nucleophilic substitution of the methanesulfonate of a 3-butyn-1-ol or 2,3-butadien-1-ol with a primary amine, or the reductive amination of an aldehyde with a primary 3-butynylamine or 2,3-butadienylamine.
  • 38
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    • Paraformaldehyde is not suitable as a source of formaldinium ion
    • Paraformaldehyde is not suitable as a source of formaldinium ion.
  • 39
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    • We observed that the use of aryl boronic esters also leads to an increase in product yields; thus, the acid moiety of electron-deficient aryl boronic acids appears to hamper the reaction
    • We observed that the use of aryl boronic esters also leads to an increase in product yields; thus, the acid moiety of electron-deficient aryl boronic acids appears to hamper the reaction.
  • 40
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    • [7] neither alkynyl amines with internal alkyne groups nor 4-pentynylamines undergo cyclization.
    • [7] neither alkynyl amines with internal alkyne groups nor 4-pentynylamines undergo cyclization.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.