Catalytic Heteroannulation for the Synthesis of Quinoline‐4‐Carboxamides Bearing Axial Chirality
作者:Xiang Zhang、Bo‐Tao Chen、Peng Gao、Rui‐Ping Song、Fang Fang、Dan‐Dan Han、You‐Dong Shao、Dao‐Juan Cheng
DOI:10.1002/adsc.202201043
日期:2022.12.20
An iron(III) triflate catalyzed Friedländer-type heteroannulation of 2-(2-aminophenyl)-N,N-dialkyl-2-oxoamides with α-methylene carbonyl derivatives has been established, allowing facile access to a range of biologically interesting quinoline-containing tertiary amides in good yields. Investigations into the configurational stability of products led to the identification of a new type of stable axially
已经建立了三氟甲磺酸铁 (III) 催化的 2-(2-氨基苯基)- N , N -二烷基-2-氧代酰胺与 α-亚甲基羰基衍生物的弗里德兰德型杂环化,从而可以轻松获得一系列具有生物学意义的喹啉-含有叔酰胺,收率高。对产品构型稳定性的研究导致鉴定出一种新型稳定的轴向手性喹啉-4-甲酰胺,带有空间要求严格的苯磺酰基 C3-取代基。随后,尝试了对映选择性催化变体。发现使用手性双恶唑啉配体的铜 (II) 催化能够提供适度的对映体控制。