期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 61, 期 1, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202110749
关键词
1; 3-dipoles; cyclizations; heterocycles; nitriles; synthetic methods
资金
- National Natural Science Foundation of China [21672032, 21802016]
- Department of Science and Technology of Jilin Province [20200201067JC]
- Education Department of Jilin Province [JJKH20201166KJ]
In this study, an alternative and scalable cyclization strategy based on NCF3-containing synthons was used to construct N-CF3 azoles. This approach allows for the divergent synthesis of N-trifluoromethylated tetrazoles, imidazoles, and 1,2,3-triazoles using various dipoles. The introduction of CF3 onto the nitrogen of heterocycles provides a direct route to such motifs, overcoming the limitations of traditional methods.
N-Trifluoromethyl azoles are valuable targets in medicinal chemistry, but their synthesis is challenging. Classical preparation of N-CF3 azoles relies on the functional group interconversions but suffers from tedious N-pre-functionalization and unfriendly agents. Introduction of the CF3 onto the nitrogen of heterocycles provides a direct route to such motifs, but the N-trifluoromethylation remains underdeveloped. Reported here is an alternative and scalable cyclization strategy based on NCF3-containing synthons for constructing N-CF3 azoles. The approach involves the N-trifluoromethylation of nitriles followed by a [3+2] cyclization between resulting N-CF3 nitrilium derivatives and 1,3-dipoles. PhICF3Cl was an effective CF3 source for the transformation. As a result, a generic platform is established to divergently synthesize N-trifluoromethylated tetrazoles, imidazoles, and 1,2,3-triazoles by using sodium azide, activated methylene isocyanides, and diazo compounds as dipoles.
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