Visible-light-induced metal-free cascade cyclization of N-arylpropiolamides to 3-phosphorylated, trifluoromethylated and thiocyanated azaspiro[4.5]trienones‡
Literature Information
Publication Date
2020-12-21
DOI
10.1039/D0QO01410A
Impact Factor
5.281
Authors
Fan-Lin Zeng, Xiao-Lan Chen, Kai Sun, Hu-Lin Zhu, Xiao-Ya Yuan, Ling-Bo Qu, Yu-Fen Zhao, Bing Yu
View Original
Abstract
Photocatalytic strategies for the preparation of 3-phosphoryl/trifluoromethyl/thiocyanato azaspiro[4.5]trienones via a radical-initiated cascade annulation reaction of N-arylpropiolamides with phosphorus reagents, 1-trifluoromethyl-1,2-benziodoxol-3(1H)-one (Togni's reagent II) or NH4SCN have been developed under blue LED irradiation at room temperature. The novel synthetic methodologies constitute the first application of 2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile (4CzIPN) as a photocatalyst for the synthesis of spiro-γ-lactam derivatives, in which the use of transition metals and a high reaction temperature could be avoided. The reactions are operationally simple, easy to scale up, and metal-free with wide reaction scope and good functional group tolerance.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-phenylpropanoic acid
CAS Number:
1217663-60-9
Molecular Formula:
C24H21NO4
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