Recent applications of 2,4,6-trichloro-1,3,5-triazine and its derivatives in organic synthesis

被引:415
作者
Blotny, Grzegorz [1 ]
机构
[1] Univ Maryland Baltimore Cty, Dept Chem & Biochem, Baltimore, MD 21250 USA
关键词
2,4,6-trichloro-1,3,5-triazine; 2-chloro-4,6-dimethoxy-s-triazine; functional group transformations;
D O I
10.1016/j.tet.2006.07.039
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of novel 2,4,6-derivatives of 1,3,5-triazine together with innovative applications of cyanuric chloride (CC) and its derivatives, in various synthetic transformations was investigated. It was found that carboxylic acids, including N-protected amino acids, can be activated with CC and subsequently reduced to their corresponding alcohols with sodium borohydride in water. It was observed that the different reactivities of chlorine atoms in CC allow sequential introduction of various substituents into a s-triazine ring using a one-pot procedure. These reagents could found applications in solid-phase synthesis by a combinatorial approach, as a template for peptides, for synthesis of noncovalently bonded supramolecular aggregates and dendrimers. 2-Choloro-4,6-dimethoxy-1,3,5-triazine (CDMT) was reported to have wide applications as a condensing reagent in peptide chemistry.
引用
收藏
页码:9507 / 9522
页数:16
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