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Synfacts 2021; 17(10): 1101
DOI: 10.1055/s-0040-1720873
DOI: 10.1055/s-0040-1720873
Metals in Synthesis
Denitrogenative Ring Shrinkage of Heterocycles
Qin H,
Cai W,
Wang S,
Guo T,
Li G,
Lu H.
*
Nanjing University, P. R. of China
N-Atom Deletion in Nitrogen Heterocycles.
Angew. Chem. Int. Ed. 2021;
60: 20678-20683
DOI: 10.1002/anie.202107356
N-Atom Deletion in Nitrogen Heterocycles.
Angew. Chem. Int. Ed. 2021;
60: 20678-20683
DOI: 10.1002/anie.202107356
Significance
Lu et al. report a versatile method for N-atom excision from N-heterocycles. Rings containing 3–20 members and various types of cyclic structures including carbocycles, O-heterocycles, and N-heterocycles were obtained in moderate to excellent yields.
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Comment
The authors propose a mechanism involving an initial N-sulfonylazidonation followed by a Curtius-type rearrangement to generate a 1,1-diazene intermediate. A second rearrangement gives a biradical intermediate that undergoes an intramolecular radical coupling reaction to give the desired product.
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Publication History
Article published online:
17 September 2021
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