Organophotoredox-Catalyzed Decarboxylative C-O/N/S Bond Formation: Access to Ampakine APIs and Quinazolinone Alkaloids

被引:0
作者
Sonavane, Sameer R. [1 ]
Kale, Tushar B. [1 ]
Bhatt, Gaurang J. [1 ]
Mhaske, Santosh B. [2 ]
机构
[1] Acad Sci & Innovat Res, Ghaziabad 201002, India
[2] CSIR Natl Chem Lab, Div Organ Chem, Pune 411008, India
关键词
CARBOXYLIC-ACIDS; TERTIARY-AMINES; DUAL CATALYSIS; PHOTOREDOX; ACTIVATION; FUNCTIONALIZATION; AMINATION;
D O I
10.1021/acs.orglett.5c00565
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This study describes a novel and general protocol featuring organophotoredox-catalyzed intramolecular decarboxylative construction of carbon-heteroatom (oxygen, nitrogen, and sulfur) bonds, enabling direct access to ampakine APIs (CX-614 and CX-554), quinazolinone alkaloids (deoxyvasicinone and mackinazolinone), and thiazinone scaffolds as well as their congeners with broad functional group tolerance and scalability. Mechanistic studies suggest a radical-polar crossover pathway via single-electron oxidation.
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页数:6
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