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Volumn , Issue 21, 2011, Pages 3552-3562

Synthesis of isoindoles via 1,3-dipolar cycloaddition of α-azido carbonyl compounds onto intramolecular alkenes and their conversion into substituted aromatic hydrocarbons

Author keywords

1,3 dipolar cycloaddition; aromatic hydrocarbons; benzynes; isoindoles; organic azides

Indexed keywords

1 ,3-DIPOLARCYCLOADDITION; ANTHRACENE DERIVATIVES; BENZYNES; CYCLOADDITION REACTION; DIMETHYL ACETYLENEDICARBOXYLATE; ISOINDOLES; ORGANIC AZIDES;

EID: 80054944872     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260221     Document Type: Article
Times cited : (17)

References (53)
  • 17
    • 79952443168 scopus 로고    scopus 로고
    • For recent reports on isoindole formation by other methods, see
    • For recent reports on isoindole formation by other methods, see: (a) Kitamura, M.; Moriyasu, Y.; Okauchi, T. Synlett 2011, 643.
    • (2011) Synlett , pp. 643
    • Kitamura, M.1    Moriyasu, Y.2    Okauchi, T.3
  • 28
    • 0004101860 scopus 로고
    • Padwa, A., Ed.; Wiley-Interscience: New York
    • (b) Padwa, A. In 1,3-Dipolar Cycloaddition Chemistry, Vol. 2; Padwa, A., Ed.; Wiley-Interscience: New York, 1984, 316.
    • (1984) 1,3-Dipolar Cycloaddition Chemistry , vol.2 , pp. 316
    • Padwa, A.1
  • 38
    • 0001365582 scopus 로고
    • and references therein
    • (l) Smith, P. A. S.; Chou, S. P. J. Org. Chem. 1981, 46, 3970; and references therein.
    • (1981) J. Org. Chem. , vol.46 , pp. 3970
    • Smith, P.A.S.1    Chou, S.P.2
  • 39
    • 0001395640 scopus 로고
    • For reports on the mechanism of the elimination of dinitrogen from triazoline intermediates with heterolytic cleavage of the N-N bond; see: (a)
    • For reports on the mechanism of the elimination of dinitrogen from triazoline intermediates with heterolytic cleavage of the N-N bond; see: (a) Shea, K. J.; Kim, J.-S. J. Am. Chem. Soc. 1992, 114, 4846.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 4846
    • Shea, K.J.1    Kim, J.-S.2
  • 41
    • 0000612741 scopus 로고
    • A radical pathway via homolytic cleavage of the N-N bond of triazoline intermediates is also proposed, for examples, see references 6c, 6g, 6h, and
    • A radical pathway via homolytic cleavage of the N-N bond of triazoline intermediates is also proposed, for examples, see references 6c, 6g, 6h, and: Broeckx, W.; Overbergh, N.; Samyn, C.; Smets, G.; L'abbé, G. Tetrahedron 1971, 27, 3527.
    • (1971) Tetrahedron , vol.27 , pp. 3527
    • Broeckx, W.1    Overbergh, N.2    Samyn, C.3    Smets, G.4    L'Abbé, G.5
  • 43
    • 80054951826 scopus 로고    scopus 로고
    • The structure of 2a was secured by X-ray crystallographic analysis (see Supporting Information). CCDC-710407 contains the supplementary crystallographic data for compound 2a. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • The structure of 2a was secured by X-ray crystallographic analysis (see Supporting Information). CCDC-710407 contains the supplementary crystallographic data for compound 2a. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/conts/retrieving. html.
  • 44
    • 80054904445 scopus 로고    scopus 로고
    • note
    • The introduction of a carbonyl moiety at C1 in isoindoles is indispensable for this isoindole formation. For an example, the reaction of 2′-vinylbenzyl azide under same reaction conditions gave a complex mixture without the desired isoindoles.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.