메뉴 건너뛰기




Volumn 52, Issue 4, 2011, Pages 544-547

A rapid synthesis of quinoxalines starting from ketones

Author keywords

Hydroxylimino ketone; 1,2 Diaminobenzene; Diketomonoxime; Microwave; Quinoxaline

Indexed keywords

1,2 PHENYLENEDIAMINE; KETONE DERIVATIVE; QUINOXALINE DERIVATIVE;

EID: 78650522514     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.116     Document Type: Article
Times cited : (45)

References (58)
  • 1
    • 78650524447 scopus 로고    scopus 로고
    • Qinoxalines: Supplement II
    • For recent reviews on quinoxalines see: D.J. Brown Qinoxalines: Supplement II E.C. Taylor, P. Wipf, The Chemistry of Heterocyclic Compounds 2004 John Wiley and Sons New Jersey
    • (2004) The Chemistry of Heterocyclic Compounds
    • Brown, D.J.1
  • 16
    • 78650522274 scopus 로고    scopus 로고
    • U. S. Patent No. WO 9951688, 1999 to The Proctor and Gamble Company, U.S.A.
    • (a) Brock, E. D.; Lewis, D. M.; Yousaf, T. I.; Harper, H. H. U. S. Patent No. WO 9951688, 1999 to The Proctor and Gamble Company, U.S.A.
    • Brock, E.D.1    Lewis, D.M.2    Yousaf, T.I.3    Harper, H.H.4
  • 17
    • 78650517900 scopus 로고    scopus 로고
    • Indian Patent No. 150/MUM/2010 (International classification: CO 9B23/14)
    • (b) Shankarling, G. S.; Sonawane, Y. A. Indian Patent No. 150/MUM/2010 (International classification: CO 9B23/14).
    • Shankarling, G.S.1    Sonawane, Y.A.2
  • 50
    • 78650519269 scopus 로고    scopus 로고
    • note
    • 27,28 (a) Neat: 1,2-Diaminobenzene (0.37 g, 3.4 mmol) and the oximino ketone (3.4 mmol) were mixed well by grinding. The mixture was taken in a sealed vial and subjected to MW irradiation. After the reaction was complete, the product was purified by passing through a short silica gel column (eluant, hexane/EtOAc = 9:1). (b) In PEG-400: A well ground mixture of 1,2-diaminobenzene (0.37 g, 3.4 mmol), oximino ketone (3.4 mmol) and PEG-400 was taken in a sealed vial and irradiated with MW. After the reaction was over, the product was obtained as mentioned in the previous case. (c) In AcOH: The same amounts of reactants as mentioned in the previous cases were ground with 2-3 drops of AcOH, and the mixture was subjected to the same procedure as mentioned earlier. The one-pot reaction: Sodium nitrite (0.617 g, 8.9 mmol) in 1 mL of water was taken in a 25 mL flask and cooled to -15 °C. Ketone (7.5 mmol) in 1 mL of PEG-400 was added, followed by concd HCl (0.33 g) over 5 min. The mixture turned green. After the colour disappeared (about 45 min), 0.74 g (6.8 mmol) of 1,2-diaminobenzene was added. The mixture was transferred to a vial and subjected to MW irradiation (9 min). After the reaction was over, the product was added to 10 mL of water and worked up in the usual way using dichloromethane for extraction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.