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Volumn , Issue 2, 2009, Pages 302-305

Heterocyclizations via TosMIC-based multicomponent reactions: A new approach to one-pot facile synthesis of substituted quinoxaline derivatives

Author keywords

Multicomponent reactions; Quinoxalines; TosMIC

Indexed keywords


EID: 62349141160     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087518     Document Type: Article
Times cited : (28)

References (56)
  • 22
    • 33845537355 scopus 로고    scopus 로고
    • Quinoxalines Supplements II
    • Taylor, E. C, Wipf, P, Eds, John Wiley & Sons: New Jersey
    • (a) Brown, D. J. Quinoxalines Supplements II, In The Chemistry of Heterocyclic Compounds; Taylor, E. C.; Wipf, P., Eds.; John Wiley & Sons: New Jersey, 2004.
    • (2004) The Chemistry of Heterocyclic Compounds
    • Brown, D.J.1
  • 51
    • 85192679045 scopus 로고    scopus 로고
    • Beck, B.; Leppert, C. A.; Mueller, B. K.; Dömling, A. QSAR Com. Sci. 2006, 25, 527.
    • (c) Beck, B.; Leppert, C. A.; Mueller, B. K.; Dömling, A. QSAR Com. Sci. 2006, 25, 527.
  • 53
    • 62349118918 scopus 로고    scopus 로고
    • Evolution of gas with alkaline pH and characteristic amine odor was detected
    • Evolution of gas with alkaline pH and characteristic amine odor was detected.
  • 54
    • 62349096771 scopus 로고    scopus 로고
    • All melting points were determined on a Büchi apparatus and are uncorrected. The 1H NMR and 13C NMR spectra were recorded on a Bruker AM 300 spectrometer in CDCl3 with TMS as internal standard. All coupling constants are given in Hz and chemical shifts are given in ppm. Typical Experimental Procedure for the Preparation of 3e: To a stirred solution of o-phenylenediamine (1a; 1.0 mmol) in toluene (20 mL, 4-chlorobenzaldehyde (1.0 mmol) was added and stirring was continued for 5 min. Then TosMIC (1.0 mmol) and DABCO (1.2 mmol) were added and the reaction mixture was heated to 80°C for 4 h. The resulting solution was initially washed with 5% HCl, then with H2O and dried. The solvent was distilled off under reduced pressure to yield the corresponding crude product mixture, which was purified by silica gel chromatography using petroleum ether-EtOAc (10:1) as eluent, to give quinoxaline 3e in 84% yield; yellow
    • 2 (240.69): C, 69.85; H, 3.74; N, 11.64. Found: C, 70.01; H, 3.83; N, 11.68.
  • 56
    • 62349098314 scopus 로고    scopus 로고
    • The multiplicities and chemical shifts of the aromatic protons have been confirmed after simulation with program SpinWorks, version 2.5, available from
    • The multiplicities and chemical shifts of the aromatic protons have been confirmed after simulation with program SpinWorks, version 2.5, available from ftp://davinci.chem.umanitoba.ca.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.