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Volumn 73, Issue 17, 2008, Pages 6943-6945

Photooxygenation of 5-dialkylamino-4-pyrrolin-3-ones. Synthesis of highly functionalized ureas, 2-oxazolidinones, and 2-oxazolinones

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONALIZED; OXAZOLIDINONES; PHOTOOXYGENATION;

EID: 51549088781     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801192z     Document Type: Article
Times cited : (5)

References (28)
  • 8
    • 0041748306 scopus 로고
    • Wasserman, H. H, Murray, R. W. Eds, Academic Press: New York, NY
    • Bartlett, P. A.; Landis, M. E. In Singlet Oxygen; Wasserman, H. H., Murray, R. W. Eds.; Academic Press: New York, NY, 1979; pp 243-286.
    • (1979) Singlet Oxygen , pp. 243-286
    • Bartlett, P.A.1    Landis, M.E.2
  • 18
    • 51549118384 scopus 로고
    • Unpublished results
    • (a) Erden, I.; Cao, W. Unpublished results, 1995.
    • (1995)
    • Erden, I.1    Cao, W.2
  • 22
    • 51549119446 scopus 로고    scopus 로고
    • In our hands, this compound is formed as a mixture of both E (13b) and Z (13a) isomers (separable by column chromatography, depending on the reaction temperature and solvent used. Moreover, we cannot account for the singlet at 3.33 ppm for the methoxy group as reported in ref 18b; rather, it appears at 3.71 ppm in the case of the (Z) isomer (13a) and 3.82 ppm in the case of 13b. Both (Z) and (E) isomers afford 18 upon photooxygenation. Upon catalytic hydrogenation, both yield the same partially reduced product 19, The experimental details are given in Supporting Information, Chemical Equation Presented
    • In our hands, this compound is formed as a mixture of both E (13b) and Z (13a) isomers (separable by column chromatography), depending on the reaction temperature and solvent used. Moreover, we cannot account for the singlet at 3.33 ppm for the methoxy group as reported in ref 18b; rather, it appears at 3.71 ppm in the case of the (Z) isomer (13a) and 3.82 ppm in the case of 13b. Both (Z) and (E) isomers afford 18 upon photooxygenation. Upon catalytic hydrogenation, both yield the same partially reduced product (19). The experimental details are given in Supporting Information. (Chemical Equation Presented)
  • 27
    • 0000992276 scopus 로고
    • Wasserman, H. H, Murray, R. W. Eds, Academic Press: New York, NY
    • Schaap, A. P.; Zaklika, K. A. In Singlet Oxygen; Wasserman, H. H., Murray, R. W. Eds.; Academic Press: New York, NY, 1979; pp 173-242.
    • (1979) Singlet Oxygen , pp. 173-242
    • Schaap, A.P.1    Zaklika, K.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.