Visible-Light-Induced Decarboxylative Annulation of α,β-Unsaturated Acids with Amines and α-Keto Acids for 2,4-Diarylquinoline Synthesis

被引:0
作者
Das, Suman [1 ]
Maiti, Souvik [1 ]
Mondal, Soumya [1 ]
Mondal, Subal [1 ]
Midya, Siba P. [2 ]
Ghosh, Pradyut [1 ]
机构
[1] Indian Assoc Cultivat Sci, Sch Chem Sci, Kolkata 700032, West Bengal, India
[2] Rammohan Coll, Dept Chem, Kolkata 700009, West Bengal, India
关键词
CARBOXYLIC-ACIDS; PHOTOREDOX CATALYSIS; 2-SUBSTITUTED QUINOLINES; REGIOSELECTIVE SYNTHESIS; CINNAMIC-ACIDS; METAL; ACCESS; CYCLIZATION; 2-ETHYNYLANILINES; PYRIDINES;
D O I
10.1021/acs.orglett.5c00099
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and sustainable approach for the synthesis of 2,4-diarylquinolines has been developed via a visible-light-promoted metal-free three-component decarboxylative annulation pathway. This one-pot protocol combines readily available feed-stock alpha,beta-unsaturated acids, aromatic amines, and alpha-keto acids in a cascade manner to access substituted quinolines under eco-benign conditions. Moreover, mechanistic insights suggest initial C-C cross coupling followed by decarboxylative 6 pi electrocyclic annulation to afford the desired products. The broad substrates scope and excellent functional group tolerance make this protocol more attractive and synthetically applicable toward the construction of complex N-heterocycles.
引用
收藏
页码:1537 / 1543
页数:7
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