1401307-35-4Relevant academic research and scientific papers
Base-catalyzed hydrogen–deuterium exchange and dehalogenation reactions of 1,2,3-triazole derivatives
Wang, Dong,Chen, Si,Wang, Jing,Astruc, Didier,Chen, Baohua
, p. 6375 - 6379 (2016/09/23)
An efficient and convenient synthesis of deuterium-labeled 1,2,3-triazoles using base-catalysis with DMSO-d6as the deuterium source was developed. A series of deuterated 1,2,3-triazoles bearing various substituents were produced by hydrogen–deuterium exchange reactions of pre-synthesized original 1,2,3-triazoles, giving high level of deuteration and high yields. The catalytic system was successfully extended to the dehalogenation and halogen–deuterium exchange procedures of iodo-functionalized 1,2,3-triazolyl derivatives. This study forms a promising basis for the future development of 1,2,3-triazolyl-containing organic derivatives, polymeric materials and biomedical molecules.
Synthesis of deuterated 1,2,3-triazoles
Akula, Hari K.,Lakshman, Mahesh K.
, p. 8896 - 8904,9 (2012/12/11)
The copper-catalyzed azide-alkyne cycloaddition (CuAAC) is a highly effective method for the selective incorporation of deuterium atom into the C-5 position of the 1,2,3-triazole structure. Reactions of alkynes and azides can be conveniently carried out in a biphasic medium of CH2Cl 2/D2O, using the CuSO4/Na ascorbate system. The mildness of the method renders it applicable to substrates of relatively high complexity, such as nucleosides. Good yields and high levels of deuterium incorporation were observed. A reaction conducted in equimolar H2O and D2O showed 2.7 times greater incorporation of hydrogen atom as compared to deuterium. This is consistent with the H+ and D + ion concentrations in H2O and D2O, respectively. With appropriately deuterated precursors, partially to fully deuterated triazoles were assembled where the final deuterium atom was incorporated in the triazole-forming step.
Synthesis of deuterated 1,2,3-triazoles
Akula, Hari K.,Lakshman, Mahesh K.
, p. 8896 - 8904 (2013/01/15)
The copper-catalyzed azide-alkyne cycloaddition (CuAAC) is a highly effective method for the selective incorporation of deuterium atom into the C-5 position of the 1,2,3-triazole structure. Reactions of alkynes and azides can be conveniently carried out in a biphasic medium of CH2Cl 2/D2O, using the CuSO4/Na ascorbate system. The mildness of the method renders it applicable to substrates of relatively high complexity, such as nucleosides. Good yields and high levels of deuterium incorporation were observed. A reaction conducted in equimolar H2O and D2O showed 2.7 times greater incorporation of hydrogen atom as compared to deuterium. This is consistent with the H+ and D + ion concentrations in H2O and D2O, respectively. With appropriately deuterated precursors, partially to fully deuterated triazoles were assembled where the final deuterium atom was incorporated in the triazole-forming step.
METHODS FOR PREPARING DEUTERATED 1,2,3-TRIAZOLES
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Page/Page column 17, (2012/10/18)
This disclosure relates to a method that involves reacting an azide with an alkyne in the presence of deuterated water and a copper-containing catalyst, thereby forming a deuterated 1,2,3-triazole.
