85770-99-6Relevant articles and documents
Influence of Annulation on the Electron Spin within the 1,2,3-Triazole Ring in Annulenotriazole Anion Radicals
Peters, Steven J.,Maybell, Donald L.
, p. 3617 - 3623 (2018)
The low temperature (-100 °C) single electron reduction of N1-phenylbenzotriazole in liquid ammonia, and the room temperature reduction of N1-phenylcyclooctatetraenotriazole in hexamethylphosphoramide, yields stable solutions of both anion radicals, which
METHODS FOR PREPARING DEUTERATED 1,2,3-TRIAZOLES
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Page/Page column 23-24, (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.
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.
Flow synthesis of organic azides and the multistep synthesis of imines and amines using a new monolithic triphenylphosphine reagent
Smith, Catherine J.,Smith, Christopher D.,Nikbin, Nikzad,Ley, Steven V.,Baxendale, Ian R.
supporting information; experimental part, p. 1927 - 1937 (2011/04/21)
Here we describe general flow processes for the synthesis of alkyl and aryl azides, and the development of a new monolithic triphenylphosphine reagent, which provides a convenient format for the use of this versatile reagent in flow. The utility of these new tools was demonstrated by their application to a flow Staudinger aza-Wittig reaction sequence. Finally, a multistep aza-Wittig, reduction and purification flow process was designed, allowing access to amine products in an automated fashion.
