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Volumn , Issue 21, 2006, Pages 3661-3669

Coupling of β-cyanocarbene-chromium complexes with 2-alkynylbenzoyl derivatives: A [5+5]-cycloaddition approach to phenanthridines

Author keywords

Alkynes; Carbene complexes; Chromium; Cycloadditions; Diels Alder reactions; Nitriles

Indexed keywords

AROMATIC COMPOUNDS; CHROMIUM COMPOUNDS; DERIVATIVES; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 33751315272     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950286     Document Type: Article
Times cited : (20)

References (35)
  • 4
  • 6
    • 0345711320 scopus 로고
    • Diels-Alder adducts have only been characterized by combustion analysis and IR spectra, and other structural alternatives were not considered: Tagmazyan, K. T.; Mkrtchyan, R. S.; Babayan, A. T. J. Org. Chem. USSR 1974, 10, 1657.
    • (1974) J. Org. Chem. USSR , vol.10 , pp. 1657
    • Tagmazyan, K.T.1    Mkrtchyan, R.S.2    Babayan, A.T.3
  • 21
    • 33751342736 scopus 로고    scopus 로고
    • note
    • 4, and (3) reaction of the aldehyde with 2-(dimethoxymethyl) phenyllithium.
  • 24
    • 84944031181 scopus 로고    scopus 로고
    • McKillop, A. E.; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Elsevier: Oxford
    • For a review of phenanthridine synthesis, see: Balasubramanian, M.; Keay, J. G. In Comprehensive Heterocyclic Chemistry II, Vol. 5; McKillop, A. E.; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Elsevier: Oxford, 1996, 245-300.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.5 , pp. 245-300
    • Balasubramanian, M.1    Keay, J.G.2
  • 25
    • 33751318774 scopus 로고    scopus 로고
    • note
    • This is a variant of a literature procedure in reference 9b. This procedure is very reliable if one is careful to cut the potassium into small pieces and if the tetramethylammonium acylate salt is prepared prior to the alkylation step. Otherwise we noted wide variances in the yields between different experimental runs.
  • 26
    • 33751311375 scopus 로고    scopus 로고
    • note
    • 2O), followed by acid chloride formation (oxalyl chloride).
  • 27
    • 33751328373 scopus 로고    scopus 로고
    • note
    • Prepared from reaction of the acid chloride (ref. 21) with aqueous dimethylamine.
  • 29
  • 30
    • 33751313661 scopus 로고
    • (Laboratories Made S.A., Spain) Span. Patent 74-423501
    • This compound is known; however, the spectral data are inaccessible: (Laboratories Made S.A., Spain) Span. Patent 74-423501; Chem. Abstr. 1976, 86, 189240.
    • (1976) Chem. Abstr. , vol.86 , pp. 189240
  • 31
    • 37049090243 scopus 로고
    • This compound was prepared from Sonogashira coupling of trimethylsilylacetylene and 2-bromobenzaldehyde followed by desilylation according to a literature procedure: Acheson, R. M.; Lee, G. C. M. J. Chem. Soc., Perkin Trans. 1 1987, 2321.
    • (1987) J. Chem. Soc., Perkin Trans. 1 , pp. 2321
    • Acheson, R.M.1    Lee, G.C.M.2
  • 32
    • 0002121207 scopus 로고    scopus 로고
    • This compound was prepared from Sonogashira coupling of hex-1-yne and 2-bromoacetophenone according to a literature procedure: Herndon, J. W.; Zhang, Y.; Wang, K. J. Organomet. Chem. 2001, 634, 1.
    • (2001) J. Organomet. Chem. , vol.634 , pp. 1
    • Herndon, J.W.1    Zhang, Y.2    Wang, K.3
  • 33
    • 33751310878 scopus 로고    scopus 로고
    • note
    • This compound was prepared from Sonogashira coupling of hex-1-yne and N,N-dimethyl-2-iodobenzamide according to a literature procedure. See reference 15.
  • 34
    • 0033588393 scopus 로고    scopus 로고
    • This compound was prepared from Sonogashira coupling of hex-1-yne and 2-iodobenzophenone according to a literature procedure: Tovar, J. D.; Swager, T. M. J. Org. Chem. 1999, 64, 6499.
    • (1999) J. Org. Chem. , vol.64 , pp. 6499
    • Tovar, J.D.1    Swager, T.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.