Copper-Catalyzed Three-Component Synthesis of 3‑Aminopyrazoles and 4‑Iminopyrimidines via β‑Alkynyl‑N‑sulfonyl Ketenimine Intermediates

3-Aminopyrazoles and 4-iminopyrimidines were efficiently prepared via copper-catalyzed three-component reactions of butadiynes, sulfonylazides, and hydrazides or imidamides. The reactions were regioselectively approached via the formation of a β-alkynyl-N-sulfonyl ketenimine intermediate which repre...

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Veröffentlicht in:Organic letters 2014-09, Vol.16 (18), p.4814-4817
Hauptverfasser: Xing, Yanpeng, Cheng, Binyu, Wang, Jing, Lu, Ping, Wang, Yanguang
Format: Artikel
Sprache:eng
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Zusammenfassung:3-Aminopyrazoles and 4-iminopyrimidines were efficiently prepared via copper-catalyzed three-component reactions of butadiynes, sulfonylazides, and hydrazides or imidamides. The reactions were regioselectively approached via the formation of a β-alkynyl-N-sulfonyl ketenimine intermediate which represented a new and effective 1,3-dielectrophilic equivalent in organic synthesis.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502302w