Application of Bis(trimethylsilyl)butadiyne in 1,2,3-Triazole Synthesis: Synthesis of (Z)-11,12-dihydro-6H-[1,2,3]triazolo[1',5':1,8]azocino[5,4-b]indole and Related Scaffolds

Authors

Peter S. Pedersen, Macalester CollegeFollow

Document Type

Honors Project On-Campus Access Only

Abstract

The 1,2,3-triazole scaffold is an important pharmacophore and a versatile substructure in biochemical, materials, and metal coordinating applications. During a study of the scope and limitations of the silver (I) and copper (I) catalyzed exhaustive desilylation of 5-trimethylsilylethynyl-4-trimethylsilyl-1,2,3-triazoles, an indole derivative serendipitously cyclized, affording a unique, unprecedented tetracyclic heterocycle, (Z)-11,12-dihydro-6H-[1,2,3]triazolo[1',5':1,8]azocino[5,4-b]indole. Several similar derivatives have since been synthesized in acceptable to excellent yields, and modifications to the precursor of cyclization have afforded more insight into the mechanism and limitations of this family of metal catalyzed alkyne hydroarylation reactions. Furthermore, these transformations demonstrate the utility and stability of 5-ethynyl-1,2,3-triazoles.

Recommended Citation

Pedersen, Peter S., "Application of Bis(trimethylsilyl)butadiyne in 1,2,3-Triazole Synthesis: Synthesis of (Z)-11,12-dihydro-6H-[1,2,3]triazolo[1',5':1,8]azocino[5,4-b]indole and Related Scaffolds" (2018). Chemistry Honors Projects. 23.
https://digitalcommons.macalester.edu/chem_honors/23