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- Title
Trifluoromethyl Rhodium‐Carbynoid in [2+1+2] Cycloadditions.
- Authors
Zhao, Wen‐Wen; Tian, Meng‐Yang; Zhou, Yi‐Lin; Liu, Lu‐Jie; Tian, Shao‐Fang; He, Chun‐Yang; Yang, Xing‐Zhi; Chen, Yong‐Zheng; Han, Wen‐Yong
- Abstract
Trifluoromethyl cationic carbyne (CF3C+:) possessing dual carbene‐carbocation behavior emulated as trifluoromethyl metal‐carbynoid (CF3C+=M) has not been explored yet, and its reaction characteristics are unknown. Herein, a novel α‐diazotrifluoroethyl sulfonium salt was prepared and used in Rh‐catalyzed three‐component [2+1+2] cycloadditions for the first time with commercially available N‐fused heteroarenes and nitriles, yielding a series of imidazo[1,5‐a] N‐heterocycles that are of interest in medicinal chemistry, in which the insertion of trifluoromethyl Rh‐carbynoid (CF3C+=Rh) into C=N bonds of N‐fused heteroarenes was involved. This strategy demonstrates synthetic applications in late‐stage modification of pharmaceuticals, construction of CD3‐containing N‐heterocycles, gram‐scale experiments, and synthesis of phosphodiesterase 10A inhibitor analog. These highly valuable and modifiable imidazo[1,5‐a] N‐heterocycles exhibit good antitumor activity in vitro, thus demonstrating their potential applications in medicinal chemistry.
- Subjects
PHOSPHODIESTERASE inhibitors; PHARMACEUTICAL chemistry; RING formation (Chemistry); HETEROARENES; ANTINEOPLASTIC agents; IMIDAZOPYRIDINES; NITRILE oxides
- Publication
Angewandte Chemie, 2024, Vol 136, Issue 13, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202318887