Synthesis of 1,6-Dihydropyridine-3-carbonitrile Derivatives via Lewis Acid-Catalyzed Annulation of Propargylic Alcohols with (E)‑3-Amino-3-phenylacrylonitriles

A novel Lewis acid-catalyzed, highly efficient, practical, and atom-economical protocol for the synthesis of functionalized 1,2-dihydropyridine-3-carbonitrile derivatives in the presence of Bi­(OTf)3 (10 mol %) in tetrahydrofuran (2.0 mL) at 80 °C for 8 h in air is described, starting from readily a...

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Veröffentlicht in:Journal of organic chemistry 2020-08, Vol.85 (15), p.9863-9875
Hauptverfasser: Du, Li-Juan, Zhang, Yuecheng, Zhang, Hong-Yu, Yin, Guohui, Wang, Xiao-Yan, Zhao, Jiquan, Han, Ya-Ping
Format: Artikel
Sprache:eng
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Zusammenfassung:A novel Lewis acid-catalyzed, highly efficient, practical, and atom-economical protocol for the synthesis of functionalized 1,2-dihydropyridine-3-carbonitrile derivatives in the presence of Bi­(OTf)3 (10 mol %) in tetrahydrofuran (2.0 mL) at 80 °C for 8 h in air is described, starting from readily accessed propargylic alcohols and (E)-3-amino-3-phenylacrylonitriles. This cycloaddition protocol, which is scalable and proceeds under mild conditions, is amenable to the gram-scale construction of valuable 1,2-dihydropyridine-3-carbonitriles. Furthermore, the good functional group compatibility and broad scope of this strategy were demonstrated by a broad range of propargylic alcohols and (E)-3-amino-3-phenylacrylonitriles, with yields ranging from 34 to 96%.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01171