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Volumn 48, Issue 52, 2007, Pages 9137-9139

3,3,6,6-Tetrachloro-2,2-dihydroxycyclohexanone as a synthetic equivalent of unavailable 3-chloro-6-hydroxy-1,2-benzoquinone: first synthesis of 4-chloro-1-hydroxyphenazines

Author keywords

1,2 Phenylenediamines; Aromatization; Dehydration; Dehydrochlorination; Phenazines

Indexed keywords

3 CHLORO 6 HYDROXY 1,2 BENZOQUINONE; 3,3,6,6 TETRACHLORO 2,2 DIHYDROXYCYCLOHEXANONE; 4 CHLORO 1 HYDROXYPHENAZINE DERIVATIVE; ALKANONE; BENZOQUINONE DERIVATIVE; PHENAZINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 36549046221     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.120     Document Type: Article
Times cited : (6)

References (32)
  • 2
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    • Katritzky A., Rees C., and Potts K. (Eds), Pergamon Press, Oxford
    • Porter A.E.A. In: Katritzky A., Rees C., and Potts K. (Eds). Comprehensive Heterocyclic Chemistry Vol. 3 (1984), Pergamon Press, Oxford 157-197
    • (1984) Comprehensive Heterocyclic Chemistry , vol.3 , pp. 157-197
    • Porter, A.E.A.1
  • 3
    • 0343074321 scopus 로고
    • Ansell M.F. (Ed), Elsevier, Amsterdam
    • McCullough K.J. In: Ansell M.F. (Ed). Rodd's Chemistry of Carbon Compounds Vol. 4, Part I J (1989), Elsevier, Amsterdam 354-416
    • (1989) Rodd's Chemistry of Carbon Compounds , vol.4 PART I J , pp. 354-416
    • McCullough, K.J.1
  • 5
    • 3142775167 scopus 로고    scopus 로고
    • Sainsbury M. (Ed), Elsevier, Amsterdam
    • Bolton R. In: Sainsbury M. (Ed). Rodd's Chemistry of Carbon Compounds Vol. 4, Part I J (2000), Elsevier, Amsterdam 162-171
    • (2000) Rodd's Chemistry of Carbon Compounds , vol.4 PART I J , pp. 162-171
    • Bolton, R.1
  • 22
    • 36549041093 scopus 로고    scopus 로고
    • note
    • Typical procedure: a mixture of 3,3,6,6-tetrachloro-2,2-dihydroxycyclohexanone 1 (3.8 mmol), the corresponding o-phenylenediamine 2 (3.8 mmol), triethylamine (14 mmol), and chloroform (50 mL) was stirred for 5 h at 45 °C. After evaporation to dryness under reduced pressure, water (150 mL) was added and the mixture was extracted with chloroform (3 × 60 mL). The combined extracts were washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure giving a solid residue that provided highly pure phenazines 3 by either direct crystallization in the appropriate solvent (3a,b) or by column chromatography (3c,d; silica gel/ethyl acetate-hexane, ratio 3:1).
  • 23
    • 36549052295 scopus 로고    scopus 로고
    • note
    • The procedure followed by us to prepare this compound is reported as Supplementary data.
  • 24
    • 36549066926 scopus 로고    scopus 로고
    • note
    • Tables of fractional atomic coordinates, thermal parameters, bond lengths and angles have been deposited at the Cambridge Crystallographic Center (CCDC 607589).
  • 32
    • 36549029393 scopus 로고    scopus 로고
    • note
    • The starting material 1 was recovered unaltered from experiments under the same preparative experimental conditions but in the absence of o-phenylenediamine.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.