Construction of functionalized naphtho[2,1-c]chromene scaffolds by Diels-Alder reaction using benzyne as dienophiles

[Display omitted] •Polycyclic compound was constructed in one-step by using benzyne as the key intermediate.•Target product dihydronaphtho[2,1-c]chromene possess great potential to be transformed to derivatives of wide application.•In the presence of DDQ, the naphthochromenes could be furnished in 9...

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Veröffentlicht in:Tetrahedron letters 2025-01, Vol.155, p.155430, Article 155430
Hauptverfasser: Lan, Chuanlin, Wang, Yingyi, Sha, Feng, Wu, Xinyan, Cui, Yian, Zheng, Yi
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Sprache:eng
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Zusammenfassung:[Display omitted] •Polycyclic compound was constructed in one-step by using benzyne as the key intermediate.•Target product dihydronaphtho[2,1-c]chromene possess great potential to be transformed to derivatives of wide application.•In the presence of DDQ, the naphthochromenes could be furnished in 96–99 % yields. In this study, a direct synthetic methodology for the construction of dihydronaphtho[2,1-c]chromene scaffold derivatives has been developed. Via the benzyne-participating Diels-Alder route, the naphtho[2,1-c]chromene skeleton possessing promising biological activity could be efficiently furnished under mild conditions.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2024.155430