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Volumn 44, Issue 17, 2003, Pages 3581-3585

Unexpected oxidation of a substituted benzo[a]phenazine: Oxidative cleavage of a double bond and formation of a macrolactone

Author keywords

[No Author keywords available]

Indexed keywords

BETA LAPACHONE; LACTONE DERIVATIVE; MACROLACTONE; OXIDE; PHENAZINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037459885     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00605-1     Document Type: Article
Times cited : (16)

References (32)
  • 11
    • 85031195979 scopus 로고    scopus 로고
    • PhD Thesis, Chemistry Institute /USP, São Carlos, SP, Brazil
    • Malta, V. R. S. PhD Thesis, Chemistry Institute /USP, São Carlos, SP, Brazil, 2000.
    • (2000)
    • Malta, V.R.S.1
  • 15
    • 85031204366 scopus 로고    scopus 로고
    • Phenazine 1 (0.314 g, 1 mmol) in a solution of dichloromethane (7 mL) was treated at room temperature with m-chloroperbenzoic acid (MCPBA) (1.72 g, 10 mmol) added in small portions. The reaction was followed by TLC. After the usual work up, the reaction product residue was submitted to column chromatography over silica gel and eluted with mixtures of hexane/ethyl acetate of increasing polarity to furnish compounds 2-4. Compound 2 was eluted with a mixture of hexane/ethyl acetate (100:1) and was recrystallized from acetone: the total yield of 2 in pure form was 27%. The two more polar products of the oxidation reaction, 3 and 4, were isolated in yields of 13% and 35%, respectively.
    • Phenazine 1 (0.314 g, 1 mmol) in a solution of dichloromethane (7 mL) was treated at room temperature with m-chloroperbenzoic acid (MCPBA) (1.72 g, 10 mmol) added in small portions. The reaction was followed by TLC. After the usual work up, the reaction product residue was submitted to column chromatography over silica gel and eluted with mixtures of hexane/ethyl acetate of increasing polarity to furnish compounds 2-4. Compound 2 was eluted with a mixture of hexane/ethyl acetate (100:1) and was recrystallized from acetone: the total yield of 2 in pure form was 27%. The two more polar products of the oxidation reaction, 3 and 4, were isolated in yields of 13% and 35%, respectively.
  • 17
    • 85031195592 scopus 로고    scopus 로고
    • 3); 1.98 (1H, ddd, J=14.8, 5.4 and 4); 2.28 (1H, ddd, J=14.8, 12.2 and 4), 2.75 (1H, ddd, J=14.6, 12.2 and 4); 3.81 (1H, ddd, J=14.6, 5.4 and 4); 7.57 (1H, td, J=7.8 and 1.6; ArH); 7.61 (1H, dd, J=7.8 and 1.6; ArH); 7.72 (1H, td, J=7.6 and 1.6; ArH); 7.83-7.87 (2H, m, 2ArH); 8.09 (1H, dd, J=7.8 and 1.6; ArH); 8.14-8.17 (2H, m, ArH).
    • 3: C, 72.82%; H, 5.24%; N, 8.09%.
  • 18
    • 85031208863 scopus 로고    scopus 로고
    • 1=0.053.
    • 1=0.053.
  • 19
    • 85031194953 scopus 로고    scopus 로고
    • 2); 201.9 (CO)
    • 4 C, 69.60%; H, 5.01%; N 7.73%.
  • 20
    • 85031193827 scopus 로고    scopus 로고
    • 1=0.057.
    • 1=0.057.
  • 21
    • 85031204665 scopus 로고    scopus 로고
    • note
    • 25.
  • 22
    • 0012864559 scopus 로고    scopus 로고
    • Delft, The Netherlands: Nonius BV
    • Nonius. COLLECT. Version 5.0. 1999;Nonius BV, Delft, The Netherlands.
    • (1999) COLLECT. Version 5.0
    • Nonius1
  • 23
    • 0031059866 scopus 로고    scopus 로고
    • Methods in Enzymology
    • C.W. Jr. Carter, Sweet R.M. New York: Academic Press
    • Otwinowski Z., Minor W. Methods in Enzymology. Carter C.W. Jr., Sweet R.M. Macromolecular Crystallography, Part A. 276:1997;307-326 Academic Press, New York.
    • (1997) Macromolecular Crystallography, Part A , vol.276 , pp. 307-326
    • Otwinowski, Z.1    Minor, W.2
  • 27
    • 85031195300 scopus 로고    scopus 로고
    • 2), 70.3 (C), 81.1 (C), 125.9 (CH), 127.4 (CH), 129.2 (CH), 129.5 (CH), 130.5 (CH), 130.6 (C), 130.7 (CH), 131.6 (CH)
    • 3 C, 72.44%; H, 5.79%; N, 8.04%.
  • 28
    • 0003467672 scopus 로고
    • For general discussion see. New York: Wiley
    • For general discussion see March J. Advanced Organic Chemistry. 1992;1177-1182 Wiley, New York.
    • (1992) Advanced Organic Chemistry , pp. 1177-1182
    • March, J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.