Rh(III)-Catalyzed Dual C–H Functionalization and C–O/C–N Annulations of Monoamide Fumarates

Pyrano­[4,3-c]­pyridine-diones, which are the key skeleton of bioactive compounds and functional materials, are usually prepared via a multistep synthesis using expensive substrates. This work demonstrates that Rh­(III)-catalyzed dual C­(sp2)–H functionalization and C–O/C–N annulation of monoamide f...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-11, Vol.87 (22), p.15547-15558
Main Authors: Han, Zhi-Jian, Zhang, Ze-Xuan, Lin, Jin-Jin, Ma, Bin, Yang, Lu-Xi, Pu, Wei-Gao, Li, Yu-Min, Chen, Hao, Da, Chao-Shan
Format: Article
Language:English
Subjects:
Catalysis
Fumarates
Molecular Structure
Pyridines - chemistry
Rhodium - chemistry
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Summary:Pyrano­[4,3-c]­pyridine-diones, which are the key skeleton of bioactive compounds and functional materials, are usually prepared via a multistep synthesis using expensive substrates. This work demonstrates that Rh­(III)-catalyzed dual C­(sp2)–H functionalization and C–O/C–N annulation of monoamide fumarates can produce pyrano­[4,3-c]­pyridine-1,5­(6H)-diones in high yield (up to 82%) in a single step. The substrates of monoamide fumarates and acetylenes are structurally simple, readily available, and inexpensive. The additive AgSbF6 effectively raised the yields. On account of easier dehydrogenation of OH in the COOH group than NH in the amide group in the reaction, the process first undergoes C–O annulation and then is succeeded by C–N annulation.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02091