ZnBr2/Oxone-mediated ipso-cyclization of N-(3-phenylprop-2-yn-1-yl)aniline

ZnBr2/Oxone-mediated ipso-cyclization of N-(3-phenylprop-2-yn-1-yl)aniline

In this work, a selective synthetic strategy towards 1-azaspiro[4.5]deca-3,6,9-trien-8-ones from N-tosyl-N-(prop-2-yn-1-yl)aniline is developed. The transformation proceeds smoothly in a mixed solvent including acetonitrile and water when ZnBr2 and Oxone are employed. Mechanism studies show that the...

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Veröffentlicht in:RSC advances 2019-10, Vol.9 (57), p.33460-33464
Hauptverfasser: Huang, Keke, Jia-Ni, Li, Qiu, Guanyinsheng, Xie, Wenlin, Liu, Jin-Biao
Format: Artikel
Sprache:eng
Schlagworte:
Acetonitrile
Aniline
Chemistry
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Zusammenfassung:In this work, a selective synthetic strategy towards 1-azaspiro[4.5]deca-3,6,9-trien-8-ones from N-tosyl-N-(prop-2-yn-1-yl)aniline is developed. The transformation proceeds smoothly in a mixed solvent including acetonitrile and water when ZnBr2 and Oxone are employed. Mechanism studies show that the reaction proceeds in a regioselective manner via a radical ipso-cyclization pathway.
ISSN:2046-2069
2046-2069
DOI:10.1039/c9ra06646b