期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 364, 期 24, 页码 4237-4243出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202201043
关键词
Axial chirality; Catalysis; Heteroannulation; Quinoline; Tertiary amide
资金
- National Natural Science Foundation of China [21602097]
- Scientific Research Foundation of Anhui University of Chinese Medicine [2021rcZD001]
- Talent Program
- [2021zrzd03]
An iron(III) triflate catalyzed Friedlander-type heteroannulation method has been developed for the synthesis of various quinoline-containing tertiary amides. The study also identified a stable axially chiral quinoline-4-carboxamide and attempted an enantioselective catalytic reaction.
An iron(III) triflate catalyzed Friedlander-type heteroannulation of 2-(2-aminophenyl)-N,N-dialkyl-2-oxoamides with alpha-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.
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