Novel Orthogonal Synthesis of a Tagged Combinatorial Triazine Library via Grignard Reaction

Jae Wook Lee; Jacqueline T. Bork; Hyung-Ho Ha; Animesh Samanta; Young-Tae Chang

doi:10.1071/CH09153

RESEARCH FRONT

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Novel Orthogonal Synthesis of a Tagged Combinatorial Triazine Library via Grignard Reaction

Jae Wook Lee ^A , Jacqueline T. Bork ^A , Hyung-Ho Ha ^B , Animesh Samanta ^B and Young-Tae Chang ^B ^C

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry, New York University, New York, NY 10003, USA.

^B Department of Chemistry, and NUS MedChem Program of Life Sciences Institute, National University of Singapore, 117543, Singapore.

^C Corresponding author. Email: chmcyt@nus.edu.sg

Australian Journal of Chemistry 62(9) 1000-1006 https://doi.org/10.1071/CH09153
Submitted: 14 March 2009 Accepted: 11 May 2009 Published: 17 September 2009

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.

Acknowledgements

This work was supported by a grant from National Institute of Health (CA-96912). We thank Dr. Matthew S. Tremblay for critical reading of the manuscript.

References

Novel Orthogonal Synthesis of a Tagged Combinatorial Triazine Library via Grignard Reaction

Abstract

Acknowledgements

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