4.7 Article

Acid-Mediated Cascade Cyclization Pathway to Indeno[2,1-c]chromen-6(7H)-ones

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JOURNAL OF ORGANIC CHEMISTRY
卷 88, 期 19, 页码 13404-13417

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.3c01459

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In this study, a triflic acid-driven dual cyclization pathway was developed to produce functionalized molecules from readily available starting materials under metal-free conditions.
Developing mild and effective synthetic strategies for producing significant molecules starting from readily available starting materials is indispensable in organic synthesis. Herein, we present a triflic acid-driven dual cyclization pathway to produce functionalized indeno[2,1-c]chromen-6(7H)-ones from simple 2-formyl (or 2-acyl) cinnamate esters and phenols. Notably, this protocol enabled the construction of two C-C bonds and one C-O bond under metal-free reaction conditions via the activation of the unreactive ester moiety in a single pot. The isolation of intermediate indenol-ester might suggest self-intramolecular cycloaddition by the proximate double bond of the enoate ester with the o-carbonyl moiety, followed by an electrophilic attack with phenol and a subsequent cyclocondensation pathway. In addition, the photophysical properties have also been examined.

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