- Synthesis of deuterated 1,2,3-triazoles
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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.
- Akula, Hari K.,Lakshman, Mahesh K.
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p. 8896 - 8904,9
(2012/12/11)
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- Synthesis of deuterated 1,2,3-triazoles
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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.
- Akula, Hari K.,Lakshman, Mahesh K.
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p. 8896 - 8904
(2013/01/15)
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- METHODS FOR PREPARING DEUTERATED 1,2,3-TRIAZOLES
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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.
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Page/Page column 22-23
(2012/10/18)
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