Catalytic Heteroannulation for the Synthesis of Quinoline-4-Carboxamides Bearing Axial Chirality,Advanced Synthesis & Catalysis

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Catalytic Heteroannulation for the Synthesis of Quinoline-4-Carboxamides Bearing Axial Chirality
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-11-11 , DOI: 10.1002/adsc.202201043
Xiang Zhang ₁ , Bo-Tao Chen ₁ , Peng Gao ₁ , Rui-Ping Song ₁ , Fang Fang ₁ , Dan-Dan Han ₂ , You-Dong Shao ₂ , Dao-Juan Cheng ₁

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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 chiral quinoline-4-carboxamide bearing a sterically demanding phenylsulfonyl C3-substituent. Subsequently, an enantioselective catalytic variant was attempted. The employment of copper(II) catalysis using a chiral bisoxazoline ligand was found to be capable of providing moderate enantiocontrol.

中文翻译：

催化杂环化合成具有轴向手性的喹啉-4-甲酰胺

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。

更新日期：2022-11-11

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