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A facile one-pot, four-component synthesis of (Z)-isomer of rhodanine-oxindole derivatives under environmentally benevolent conditions

Moghaddam, F. M ; Sharif University of Technology | 2022

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  1. Type of Document: Article
  2. DOI: 10.1080/00397911.2021.2008445
  3. Publisher: Taylor and Francis Ltd , 2022
  4. Abstract:
  5. Herein, an efficient and sustainable one-pot, four-component access to rhodanine-oxindole derivatives is achieved by a reaction between primary amines, carbon disulfide, ethyl chloroacetate, and cyano-substituted alkenyl oxindoles. The reaction was conducted without any harsh conditions as well as exhausting workup in polyethylene glycol (PEG) as a green solvent at room temperature and delivered rhodanine-oxindole products in high yield. This publication is the first easy protocol to be reported for the rapid construction of new rhodanine-oxindole derivatives at room temperature without harsh conditions and via multicomponent reaction. © 2021 Taylor & Francis Group, LLC
  6. Keywords:
  7. Dithiocarbamate ; Green synthesis ; Multi-component reaction ; Oxindole ; Rhodanine ; 2 [1 allyl 3 (3 benzyl 4 hydroxy 2 thioxo 2,3 dihydrothiazol 5 yl) 2 oxoindolin 3 yl]but 3 ynenitrile ; Alkenyl group ; Amine ; Aniline ; Benzylamine ; Carbon disulfide ; Chloroacetic acid ; Ethylamine ; Heterocyclic compound ; Macrogol ; Methylamine ; Oxindole derivative ; Rhodanine oxindole derivative ; Unclassified drug ; Article ; Carbon nuclear magnetic resonance ; Controlled study ; Crystal structure ; Drug mixture ; Drug structure ; Drug synthesis ; Elimination reaction ; Green chemistry ; Infrared spectroscopy ; Isomer ; Michael addition ; One pot synthesis ; Proton nuclear magnetic resonance ; Quantum yield ; Reaction optimization ; Room temperature ; Stereospecificity ; Substitution reaction ; X ray crystallography
  8. Source: Synthetic Communications ; Volume 52, Issue 2 , 2022 , Pages 175-184 ; 00397911 (ISSN)
  9. URL: https://www.tandfonline.com/doi/abs/10.1080/00397911.2021.2008445