1. Novel Orthogonal Synthesis of a Tagged Combinatorial Triazine Library via Grignard Reaction
- Author
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Jacqueline T. Bork, Animesh Samanta, Hyung-Ho Ha, Young-Tae Chang, and Jae Wook Lee
- Subjects
chemistry.chemical_compound ,Solid-phase synthesis ,chemistry ,Biocatalysis ,Aryl ,Cyanuric chloride ,Grignard reaction ,General Chemistry ,Linker ,Combinatorial chemistry ,Amination ,Triazine - Abstract
To expand the diversity of 1,3,5-triazine libraries to aryl and alkyl functionalities through the C–C bond, we employed a novel orthogonal synthesis via Grignard monoalkylation or monoarylation of cyanuric chloride in solution to prepare aryl- or alkyl-substituted triazine building blocks. These aryl- or alkyl-substituted triazine building blocks were captured by a resin-bound amine, followed by amination and acidic cleavage with high purity. Herein, we demonstrate a novel orthogonal synthesis of a tagged aryl- and alkyl-triazine library on solid support, utilizing building blocks prepared via Grignard reaction in solution. Through incorporation of a triethylene glycol linker at one of the alternate sites on the triazine scaffold we explored an intrinsic tagged library approach.
- Published
- 2009