Brønsted Acid Catalyzed and NIS-Promoted Cyclization of Diynones: Selective Synthesis of 4‑Pyrone, 4‑Pyridone, and 3‑Pyrrolone Derivatives

Brønsted acid catalyzed tandem cyclization was found to be highly effective for the preparation of a series of polysubstituted 4-pyrones from diynones (yield up to 99%). 4-Pyridone and 3-pyrrolone derivatives were also selectively synthesized by employing NIS and/or Brønsted acid. NIS as an electrop...

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Veröffentlicht in:Journal of organic chemistry 2013-12, Vol.78 (23), p.12018-12028
Hauptverfasser: Qiu, Yi-Feng, Yang, Fang, Qiu, Zi-Hang, Zhong, Mei-Jin, Wang, Li-Jing, Ye, Yu-Ying, Song, Bo, Liang, Yong-Min
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Sprache:eng
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Zusammenfassung:Brønsted acid catalyzed tandem cyclization was found to be highly effective for the preparation of a series of polysubstituted 4-pyrones from diynones (yield up to 99%). 4-Pyridone and 3-pyrrolone derivatives were also selectively synthesized by employing NIS and/or Brønsted acid. NIS as an electrophilic reagent could promote these reactions efficiently and rapidly under very mild reaction conditions.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo402055a