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.
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.
Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, China.
Zhi-Qiang
ZQ
Wang
Yong
Y
Lei
Ming-Bo
MB
Zhou
Guo-Xiang
GX
Chen
Ren-Jie
RJ
Song
Ye-Xiang
YX
Xie
Jin-Heng
JH
Li
D000480:Alkynes / Q000737:chemistry; D001578:Benzopyrans / Q000138:chemical synthesis*; D004980:Ethane / Q000737:chemistry*; D007192:Indenes / Q000737:chemistry*; D007501:Iron / Q000737:chemistry*; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*
D000480:Alkynes; D001578:Benzopyrans; D007192:Indenes; D009284:Naphthols; C093581:indene; D007501:Iron; D004980:Ethane