Pd-Catalyzed Tandem Approach for 1,2,3-Triazolo-azepine Fused Benzosuberenes and 1,2,3-Triazolobenzazepines Synthesis

• DOI: 10.1021/acs.joc.4c02454
• Publication Date: 2025-01-31T19:54:52Z
• Authors: Ashish Kumar; Poonam Sharma; Sheetal; Navneet Sharma; Kousik Giri; Pralay Das
• Keywords: Azepine; Tandem; Functional group

Herein, a highly efficient palladium-catalyzed tandem approach for the synthesis of 1,2,3-triazolo-azepine-fused benzosuberenes (TAABS) has been developed first time with vinyl bromide and internal alkynes as starting precursors. The given reaction proceeded under ligand- additive-free conditions via sequential carbopalladation, followed by intramolecular electrophilic substitution. Also, protocol good functional group tolerance, wherein range sterically hindered TAABS analogues synthesized in appreciable yields. In addition, methodology was also extended 1,2.3-triazolobenzazepines from triazole-bearing aryl iodides alkynes. present operates relatively milder comparatively shorter time. Furthermore, computational studies were performed to validate proposed mechanistic pathways. Additionally, is applicable gram-scale analogues.