• Title/Summary/Keyword: Isatins

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Synthesis and Fragmentation Behavior Study of n-alkyl/benzyl Isatin Derivatives Present in Small/Complex Molecules: Precursor for the Preparation of Biological Active Heterocycles

  • Kadi, Adnan A.;Al-Shakliah, Nasser S.;Motiur Rahman, A. F. M.
    • Mass Spectrometry Letters
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    • v.6 no.3
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    • pp.65-70
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    • 2015
  • N-Alkyl/benzyl substituted isatin derivatives are intermediates and synthetic precursors for the preparation of biological active heterocycles. N-alkyl/benzyl isatins have showed various biological activities, such as cytotoxicity, antiviral, caspase inhibition, cannabinoid receptor 2 agonists for the treatment of neuropathic pain, etc. In this study, N-alkyl/benzyl isatin derivatives were synthesized from isatin and alkyl/benzyl halides in presence of K2CO3 in DMF and excellent to quantitative yields (~95%) were obtained. Isatins and benzyl-isatins were condensed with fluorescein hydrazide to form fluorescein hydrazone. All the compounds were subjected to their fragmentation behavior study using LC/MSn. N-Alkyl substituted isatin derivatives fragmented at nitrogen-carbon (N-C) bond, hence gave daughter ion as [RN+H]+. Whereas, N-benzyl substituted isatin derivatives fragmented at carbon-carbon (C-C) bond of alkyl chain which linked with nitrogen molecules, therefore gave N-methyl fragments [RNCH2]+. This study demonstrated that, isatin moiety present in a small/large molecule or in a matrix of reaction mixture with/without N-alkyl/benzyl substituents can be identified by mass spectroscopic fragmentation behavior study.

Synthesis of 3-Aryl-3-hydroxypyrrolidin-2-ones and 2-Benzyl-9b-hydroxy-3,3a,5,9b-tetrahydro-2H-pyrrolo[3,4-c]quinoline-1,4-dione Derivatives from the Baylis-Hillman Adducts of Isatins

  • Kim, Seung Chan;Lee, Ka Young;Gowrisankar, Saravanan;Kim, Jae Nyoung
    • Bulletin of the Korean Chemical Society
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    • v.27 no.8
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    • pp.1133-1139
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    • 2006
  • We prepared 3-aryl-3-hydroxypyrrolidin-2-one and tricyclic 2-benzyl-9b-hydroxy-3,3a,5,9b-tetrahydro-2H-pyrrolo[3,4-c]quinoline-1,4-dione derivatives starting from the Baylis-Hillman adducts of isatin derivatives.

Synthesis of Oxindole and Isatin Derivatives (옥시인돌과 이사틴 유도체들의 합성)

  • Kim, Byung-SO
    • Journal of the Korean Society of Industry Convergence
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    • v.6 no.2
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    • pp.123-129
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    • 2003
  • Oxindoles(6a-g) are obtained by rhodium(II)-catalyzed Wolff rearrangement of diazoquinolinediones in moderate yields. Treatment of 6a-g oxindole derivatives reacted with CAN in acetonitrile at room temperature to gave 7a-g isatins in good yields. The structures of these compound were identified by MP, IR and NMR-spectra.

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An Efficient Method for Multicomponent Synthesis of Spiro[4H-pyran-oxindole] Derivatives Catalyzed by Magnesium Perchlorate

  • Wu, Chunlei;Shen, Runpu;Chen, Jianhui;Hu, Chunqi
    • Bulletin of the Korean Chemical Society
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    • v.34 no.8
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    • pp.2431-2435
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    • 2013
  • A simple and efficient method for the synthesis of spiro[4H-pyran-oxindole] derivatives by means of three-component reactions between isatins, malononitrile or ethyl cyano-acetate, and 1,3-dicarbonyl compounds in the presence of catalytic amount of magnesium perchlorate in 50% aqueous ethanol medium has been described.