4.2 Article

ONE-POT SYNTHESIS OF FUSED 2-PYRIDONES FROM HETEROARYLACRYLIC ACID VIA CURTIUS REARRANGEMENT AND MICROWAVE-ASSISTED THERMAL ELECTROCYCLIZATION

Journal

HETEROCYCLES
Volume 95, Issue 1, Pages 251-267

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-16-S(S)13

Keywords

Thermal Electrocyclization Reaction; Microwave Irradiation; 2-Azahexatriene; Fused Pyridine; One-Pot Reaction

Funding

  1. Japan Society for the Promotion of Science [15K07880]
  2. Grants-in-Aid for Scientific Research [15K07880] Funding Source: KAKEN

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We investigated the one-pot synthesis of several fused 2-pyridone ring systems based on a Curtius rearrangement, followed by a microwave-assisted thermal electrocyclization of a 2-aza-6 pi-electron system including isocyanate. We synthesized seven heterocyclic compounds containing a fused 2-pyridone ring. In these results, the one-pot synthesis of fused 2-pyridone ring system 5 from (E)-acrylic acids 1 under microwave irradiation conditions was more effective than the conventional reaction conditions in terms of the yield and the reaction time.

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