In:
Angewandte Chemie International Edition, Wiley, Vol. 63, No. 13 ( 2024-03-22)
Abstract:
Trifluoromethyl cationic carbyne (CF 3 C + :) possessing dual carbene‐carbocation behavior emulated as trifluoromethyl metal‐carbynoid (CF 3 C + =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 (CF 3 C + =Rh) into C=N bonds of N ‐fused heteroarenes was involved. This strategy demonstrates synthetic applications in late‐stage modification of pharmaceuticals, construction of CD 3 ‐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.
Type of Medium:
Online Resource
ISSN:
1433-7851
,
1521-3773
DOI:
10.1002/anie.202318887
Language:
English
Publisher:
Wiley
Publication Date:
2024
detail.hit.zdb_id:
2011836-3
detail.hit.zdb_id:
123227-7
