The photochemistry of indomethacin

作者: Alan C. Weedon , David F. Wong

DOI: 10.1016/1010-6030(91)85071-N

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摘要: Abstract The photochemistry of the anti-inflammatory drug Indomethacin (N-(para-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid (1) was investigated. Unlike previously examined N-carbonyl-substituted indoles, which undergo photo-Fries rearrangement and photocycloaddition to alkenes, yields products derived from photochemical decarboxylation acetic side chain. also exhibits unusual long wavelength fluorescence is ascribed a charge transfer singlet excited state.

参考文章(10)
H. Kämmerer, G. Happel, V. Böhmer, HALOGEN AS A READILY CLEAVABLE PROTECTIVE GROUP FOR REACTIVE POSITIONS IN PHENOLS AND PHENOLIC COMPOUNDS Organic Preparations and Procedures International. ,vol. 8, pp. 245- 248 ,(1976) , 10.1080/00304947609355637
Bimsara W. Disanayaka, Alan C. Weedon, The mechanism of the photochemical cycloaddition reaction of N-benzoylindole with cyclopentene Canadian Journal of Chemistry. ,vol. 68, pp. 1685- 1692 ,(1990) , 10.1139/V90-262
Iain. McAuley, Erik. Krogh, Peter. Wan, Carbanion intermediates in the photodecarboxylation of benzannelated acetic acids in aqueous solution Journal of the American Chemical Society. ,vol. 110, pp. 600- 602 ,(1988) , 10.1021/JA00210A049
Bimsara W. Disanayaka, Alan C. Weedon, Charge transfer fluorescence of some N-benzoylindoles Canadian Journal of Chemistry. ,vol. 65, pp. 245- 250 ,(1987) , 10.1139/V87-040
Andreas Rudolph, Alan C. Weedon, Acid catalysis of the photochemical deconjugation reaction of 3-alkyl-2-cyclohexenones Journal of the American Chemical Society. ,vol. 111, pp. 8756- 8757 ,(1989) , 10.1021/JA00205A048
David L. Oldroyd, Alan C. Weedon, Solvent- and wavelength-dependent photochemistry of N-benzoylindole and N-ethoxycarbonylindole Journal of Photochemistry and Photobiology A: Chemistry. ,vol. 57, pp. 207- 216 ,(1991) , 10.1016/1010-6030(91)85016-A
David R. Julian, Robert Foster, Photoaddition of olefins to indoles: synthesis of tetrahydro-1H-cyclobut[b]indoles Journal of the Chemical Society, Chemical Communications. pp. 311- 312 ,(1973) , 10.1039/C39730000311
Masazumi Ikeda, Kazunori Ohno, Shin-ichiro Mohri, Masami Takahashi, Yasumitsu Tamura, Regio- and stereo-chemical aspects of [2+2]photocycloaddition between 1-benzoylindoles and olefins Journal of The Chemical Society-perkin Transactions 1. ,vol. 15, pp. 405- 412 ,(1984) , 10.1039/P19840000405
William Carruthers, Nigel Evans, Photolysis of 1-benzoyl- and 1- and 3-o-lodobenzoyl-indole Journal of the Chemical Society, Perkin Transactions 1. ,vol. 5, pp. 1523- 1525 ,(1974) , 10.1039/P19740001523