메뉴 건너뛰기




Volumn 7, Issue 12, 2001, Pages 2617-2627

Synthesis of radialene-shaped pyrroles by multiple-anion-capture reactions of 1,3-dianions

Author keywords

Anions; Cyclization; Multicomponent reactions; Quantum chemical calculations; Regioselectivity

Indexed keywords

ANION; NITRILE; OXALIC ACID DERIVATIVE; PYRROLE DERIVATIVE;

EID: 0035907735     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010618)7:12<2617::AID-CHEM26170>3.0.CO;2-F     Document Type: Article
Times cited : (16)

References (80)
  • 1
    • 0001133088 scopus 로고
    • For reviews on radialenes, see: a) H. Hopf, G. Maas, Angew. Chem. 1992, 104, 953;
    • (1992) Angew. Chem. , vol.104 , pp. 953
    • Hopf, H.1    Maas, G.2
  • 15
    • 33847582844 scopus 로고
    • Hoechst AG, BP 1-478-643, 1977
    • b) Hoechst AG, BP 1-478-643, 1977; [Chem. Abstr. 1918, 88, 168480].
    • (1918) Chem. Abstr. , vol.88 , pp. 168480
  • 26
    • 0001573936 scopus 로고    scopus 로고
    • For recent cyclization reactions of dianions and dianion equivalents from our laboratory, see: a) P. Langer, M. Stoll, Angew. Chem. 1999, 111, 1919;
    • (1999) Angew. Chem. , vol.111 , pp. 1919
    • Langer, P.1    Stoll, M.2
  • 59
    • 0001250164 scopus 로고    scopus 로고
    • For a preliminary communication of parts of this work, see: P. Langer, M. Döring, Synlett 1998, 399.
    • (1998) Synlett , pp. 399
    • Langer, P.1    Döring, M.2
  • 61
    • 0025865630 scopus 로고
    • b) C. M. Thompson, D. Green, Tetrahedron 1991, 47, 4223. We refer to ambident dianions as systems bearing two delocalized negative charges, in the generation of which at least one abstraction of a proton attached to a carbon is involved.
    • (1991) Tetrahedron , vol.47 , pp. 4223
    • Thompson, C.M.1    Green, D.2
  • 62
    • 0027515052 scopus 로고
    • For the extrusion of CO in the reaction of 1,2-diols with oxalyl chloride, see: T. Iida, T. Itaya, Tetrahedron 1993, 49, 10 511.
    • (1993) Tetrahedron , vol.49 , pp. 10511
    • Iida, T.1    Itaya, T.2
  • 66
    • 37049098406 scopus 로고
    • Studies have been reported on the tautomerism of 3-acetyltetramic acids. These compounds can occur in enolic tautomers A/B and C/D, in addition to tautomers A-D. Tautomers A/B and C/D are rapidly interconverted, and the NMR spectra show signals, in which chemical shifts are weighted averages of those tautomers. The interconversion between tautomers A-D is a slow process on the NMR timescale, and separate NMR signals are detected: a) M. J. Nolte, P. S. Steyn, P. L. Wessels, J. Chem. Soc. Perkin Trans. 1 1980, 1057;
    • (1980) J. Chem. Soc. Perkin Trans. 1 , pp. 1057
    • Nolte, M.J.1    Steyn, P.S.2    Wessels, P.L.3
  • 70
    • 0000286244 scopus 로고
    • An oxa-analogue of this heterocyclic system has been previously prepared: G. Walker, B. N. Weaver, J. Org. Chem. 1961, 26, 4441.
    • (1961) J. Org. Chem. , vol.26 , pp. 4441
    • Walker, G.1    Weaver, B.N.2
  • 73
    • 0004719069 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-405947 (6a), CCDC-405948 (10a), and CCDC-132023 (13a). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
  • 76
    • 0004150157 scopus 로고
    • University of Göttingen
    • G. M. Sheldrick, SHELXL-93, University of Göttingen, 1993.
    • (1993) SHELXL-93
    • Sheldrick, G.M.1
  • 77
    • 33847580961 scopus 로고    scopus 로고
    • AMI
    • (Eds.: Rv. R. Schleyer, N. L. Allinger, T. Clark, J. Gasteiger, P. Kollman, H. F. Schaefer III, P. R. Schreiner), Wiley, Chichester
    • J. J. P. Stewart, AMI in The Encyclopedia of Computational Chemistry (Eds.: Rv. R. Schleyer, N. L. Allinger, T. Clark, J. Gasteiger, P. Kollman, H. F. Schaefer III, P. R. Schreiner), Wiley, Chichester, 1998, p. 2574.
    • (1998) The Encyclopedia of Computational Chemistry , pp. 2574
    • Stewart, J.J.P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.