Iron-mediated [3 + 2] or [3 + 3] annulation of 2-(2-(ethynyl)phenoxy)-1-arylethanones: selective synthesis of indeno[1,2-c]chromenes and 5H-naphtho[1,2-c]chromenes |
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Authors: | Wang Zhi-Qiang Lei Yong Zhou Ming-Bo Chen Guo-Xiang Song Ren-Jie Xie Ye-Xiang Li Jin-Heng |
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Affiliation: | Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, China. |
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Abstract: | An iron-mediated tandem annulation strategy has been developed for the synthesis of numerous functional indeno[1,2-c]chromenes and 5H-naphtho[1,2-c]chromenes. This work is the first to disclose an iron-mediated method through sequential electrophilic addition of a ketone to an alkyne and annulation tandem reaction. Importantly, a halide is introduced into the products by a ring-opening process among the annulation of alkynylcyclopropanes, which makes the methodology more attractive for organic synthesis. |
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