SynOpen (May 2021)

Synthesis of Functionalized Bicyclic Pyridones Containing the Dithiocarbamate Group Using Thioazlactones, Diamines, and Nitroketene Dithioacetal

  • Marziyeh Saeedi,
  • Maryam Khoshdoun,
  • Salman Taheri,
  • Azim Ziyaei Halimehjani,
  • Aliasghar Mohammadi,
  • Mohammad Reza Halvagar,
  • Vahid Amani

DOI
https://doi.org/10.1055/a-1492-9229
Journal volume & issue
Vol. 05, no. 02
pp. 108 – 113

Abstract

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An efficient method for the synthesis of highly substituted bicyclic pyridone derivatives containing the dithiocarbamate group is reported via a one-pot three-component reaction of 2-(alkylthio)thio­azlactones, diamines, and nitroketene dithioacetal in EtOH under catalyst-free conditions. The reaction proceeds via a domino amidation–­intramolecular 1,4-addition-type Friedel–Crafts alkylation reaction to afford the corresponding fused bicyclic pyridones with high yields and diastereoselectivity.

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