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Paper | Special issue | Vol 95, No. 1, 2017, pp.251-267
Published online, 19th October, 2016
DOI: 10.3987/COM-16-S(S)13
■ One-Pot Synthesis of Fused 2-Pyridones from Heteroarylacrylic Acid via Curtius Rearrangement and Microwave-Assisted Thermal Electrocyclization

Takashi Nishiyama, Noriyuki Hatae, Kaori Hayashi, Manami Obata, Kimiko Taninaka, Masahiro Yamane, Shota Oda, Takumi Abe, Minoru Ishikura, Satoshi Hibino, and Tominari Choshi*

*Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan

Abstract

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-6π-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.