Rapid construction of cyclopenta[]naphthalene frameworks from propargylic alcohol tethered methylenecyclopropanes

We have developed a new synthetic methodology for the rapid construction of cyclopenta[ b ]naphthalene frameworks from the reaction of propargylic alcohol tethered methylenecyclopropanes with mesyl chloride in the presence of triethylamine through cascade cyclization. The reaction can be performed u...

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Veröffentlicht in:Organic & biomolecular chemistry 2020-09, Vol.18 (37), p.7396-74
Hauptverfasser: Wei, Hao-Zhao, Li, Quan-Zhe, Wei, Yin, Shi, Min
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Sprache:eng
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Zusammenfassung:We have developed a new synthetic methodology for the rapid construction of cyclopenta[ b ]naphthalene frameworks from the reaction of propargylic alcohol tethered methylenecyclopropanes with mesyl chloride in the presence of triethylamine through cascade cyclization. The reaction can be performed under mild conditions without the use of transition metals, affording the target products in moderate to good yields, and this cyclization reaction process can be scaled up to a gram-scale synthesis. We have developed a novel synthetic methodology to rapidly construct cyclopenta[ b ]naphthalene frameworks from propargylic alcohol tethered methylenecyclopropanes and MsCl through cascade cyclization.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob01732a