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 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.

Citation

Zhi-Jian Han, Ze-Xuan Zhang, Jin-Jin Lin, Bin Ma, Lu-Xi Yang, Wei-Gao Pu, Yu-Min Li, Hao Chen, Chao-Shan Da. Rh(III)-Catalyzed Dual C-H Functionalization and C-O/C-N Annulations of Monoamide Fumarates. The Journal of organic chemistry. 2022 Nov 18;87(22):15547-15558

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PMID: 36306342

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