메뉴 건너뛰기




Volumn 61, Issue 8, 1996, Pages 2774-2779

Nitrosation of phenolic substrates under mildly basic conditions: Selective preparation of p-quinone monooximes and their antiviral activities

Author keywords

[No Author keywords available]

Indexed keywords

8 QUINOLINOL; ACICLOVIR; ANTIVIRUS AGENT; DIDANOSINE; NITROSO DERIVATIVE; QUINONE DERIVATIVE; ZIDOVUDINE;

EID: 0029893067     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951873s     Document Type: Article
Times cited : (29)

References (30)
  • 1
    • 0001012180 scopus 로고
    • Barton, D. Ollis W. D. Eds.; Pergamon Press: Oxford
    • Coombes, R. G. In Comprehensive Organic Chemistry; Barton, D. Ollis W. D. Eds.; Pergamon Press: Oxford, 1979: Vol. 2, pp 305-381.
    • (1979) Comprehensive Organic Chemistry , vol.2 , pp. 305-381
    • Coombes, R.G.1
  • 2
    • 15844405360 scopus 로고    scopus 로고
    • note
    • 1
  • 9
    • 15844425736 scopus 로고
    • 1H NMR spectra (see the Experimental Section).
    • (1990) Chem. Abstr. , vol.112
  • 11
    • 15844390175 scopus 로고    scopus 로고
    • note
    • MO calculations were performed by the AM-1 method with CAChe ver. 3.6.
  • 13
    • 15844373260 scopus 로고    scopus 로고
    • note
    • 1
  • 15
    • 15844393793 scopus 로고    scopus 로고
    • Preparation of this naphthol will be reported elswhere
    • Preparation of this naphthol will be reported elswhere.
  • 16
    • 15844431276 scopus 로고    scopus 로고
    • note
    • 4: C, 55.96; H, 3.65; N, 7.25. Found: C, 56.04; H, 3.42; N, 7 12.
  • 17
    • 15844413285 scopus 로고    scopus 로고
    • note
    • 3, under the conditions of basic nitrosation resulted in complete recovery of the starting material.
  • 18
    • 15844400414 scopus 로고    scopus 로고
    • note
    • 6) δ 6.15 (d, 3/4 × 1H, J = 9.8 Hz), 6.42 (d, 1/4 × 1H, J = 9.8 Hz), 7.19 (d, 3/4 × 1H, J = 9.8 Hz), 7.52 (dd, 1/4 × 1H, J = 8.5, 4.2 Hz), 7.54 (dd, 3/4 × 1H, J = 8.5, 4.2 Hz), 8.19 (d, 1/4 × 1H. J = 9.8 Hz), 8.60 (dd, 1/4 × 1H, J = 4.2, 1.7 Hz), 8.62 (dd, 3/4 × 1H, J = 4.2, 1.7 Hz), 9.29 (dd, 3/4 × 1H, J = 8.5, 1.7 Hz), 9.83 (dd, 1/4 × 1H, J = 8.5, 1.7 Hz).
  • 19
    • 0346259156 scopus 로고
    • The Baudisch reaction, in which a chelate structure could govern the orientation of substitution, is used for the regioselective introduction of a nitroso group into the ortho position of the OH group in phenols. (a) Cronheim, G. J. Org. Chem. 1947, 12, 7.
    • (1947) J. Org. Chem. , vol.12 , pp. 7
    • Cronheim, G.1
  • 28
    • 15844401504 scopus 로고
    • and deprotection of the benzyl group by hydrogenolysis
    • The starting benzofuran was prepared by three successive reactions of the propargyl etherification of 2-(benzyloxy)phenol, the cesium-mediated Claisen rearrangement (Ishii, H.; Ishikawa, T.; Ueki, S.; Takeda, S.; Suzuki, M. Chem. Pharm. Bull. 1992, 40, 1123), and deprotection of the benzyl group by hydrogenolysis. Ishikawa, T.; Watanabe, T.; Oku, Y.; Takami, A. unpublished results.
    • (1992) Chem. Pharm. Bull. , vol.40 , pp. 1123
    • Ishii, H.1    Ishikawa, T.2    Ueki, S.3    Takeda, S.4    Suzuki, M.5
  • 29
    • 15844373650 scopus 로고    scopus 로고
    • unpublished results
    • The starting benzofuran was prepared by three successive reactions of the propargyl etherification of 2-(benzyloxy)phenol, the cesium-mediated Claisen rearrangement (Ishii, H.; Ishikawa, T.; Ueki, S.; Takeda, S.; Suzuki, M. Chem. Pharm. Bull. 1992, 40, 1123), and deprotection of the benzyl group by hydrogenolysis. Ishikawa, T.; Watanabe, T.; Oku, Y.; Takami, A. unpublished results.
    • Ishikawa, T.1    Watanabe, T.2    Oku, Y.3    Takami, A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.