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Four-Component Heterocyclization Reaction for the One-Pot Synthesis of 2,4-Dichloro-Substituted Pyrano/Furo[2,3-d]pyrimidines in an Environmentally Benign Procedure Mediated by Ceric Ammonium Nitrate in Phosphorus Ionic Liquid

Bahrami, G ; Sharif University of Technology | 2023

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  1. Type of Document: Article
  2. DOI: 10.1080/10406638.2022.2030769
  3. Publisher: Taylor and Francis Ltd , 2023
  4. Abstract:
  5. An unprecedented and efficient methodology for the synthesis of 2,4-dichloro-substituted pyrano[2,3-d]pyrimidines and 2,4-dichloro-substituted furo[2,3-d]-pyrimidines is conducted through the one-pot heterocyclization and four-component condensation of acetophenone derivatives, various aromatic aldehydes/potassium iodide, malononitrile, and carbon tetrachloride. The cerium(IV) ammonium nitrate (CAN) was used as a single electron oxidant and ionic liquid (HTPB) as a green promoter under mild conditions at ambient temperature for synthesizing pyrimidine derivatives in high yields. A possible radical mechanism is proposed for these transformations. CAN is found to play an essential role in each step of the reaction. The major advantages of this methodology are experimentally simplicity, environmentally benign, nontoxic, and inexpensive catalyst, excellent yields, and short reaction times. © 2022 Taylor & Francis Group, LLC
  6. Keywords:
  7. 2,4-dichloro-furo[2,3-d]-pyrimidine ; 2,4-dichloro-pyrano[2,3-d]pyrimidine ; Ceric ammonium nitrate ; Four-component ; Green chemistry ; Heterocyclization
  8. Source: Polycyclic Aromatic Compounds ; Volume 43, Issue 2 , 2023 , Pages 1566-1574 ; 10406638 (ISSN)
  9. URL: https://www.tandfonline.com/doi/abs/10.1080/10406638.2022.2030769