Combinatorial Solid-Phase Synthesis of 6-Aryl-1,3,5-triazines via Suzuki Coupling
Jae Wook Lee A , Hyung-Ho Ha B C , Marc Vendrell D , Jacqueline T. Bork A and Young-Tae Chang B D E
+ Author Affiliations
- Author Affiliations
A Department of Chemistry, New York University, New York, NY 10003, USA.
B Department of Chemistry and Medchem Program of Life Sciences Institute, National University of Singapore, 117543, Singapore.
C College of Pharmacy, Sunchon National University, Suncheon, 570-742, Korea.
D Singapore Bioimaging Consortium, Agency for Science, Technology and Research (A*STAR), Singapore, 138667, Singapore.
E Corresponding author. Email: chmcyt@nus.edu.sg
Australian Journal of Chemistry 64(5) 540-544 https://doi.org/10.1071/CH11034
Submitted: 20 January 2011 Accepted: 17 February 2011 Published: 30 May 2011
Abstract
A synthetic methodology to prepare collections of trisubstituted aryl 1,3,5-triazines with broad structural diversity via Suzuki coupling has been developed. We first optimized the combinatorial derivatization of the triazine core using Suzuki cross-coupling. Second, in order to further expand the methodology for the preparation of negatively charged triazines, we adapted this approach to polymer-supported amino acids and prepared aryl triazines with different charge distribution. With a collection of 160 aryl triazine derivatives in good purities and without any purification step, we proved the viability of this orthogonal scheme for the preparation of triazine libraries using amine/amino acid-captured solid supports and Suzuki cross-coupling.
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