233760-07-1Relevant academic research and scientific papers
Regioselective α-Deuteration of Michael Acceptors Mediated by Isopropylamine in D2O/AcOD
Landge, Vinod G.,Shrestha, Kendra K.,Grant, Aaron J.,Young, Michael C.
supporting information, p. 9745 - 9750 (2020/12/21)
Site-specific hydrogen/deuterium exchange is an important method to access deuterated compounds for chemical and biological studies. Herein is reported the first method for the regioselective α-deuteration of enals and enones. The transformation features D2O and AcOD as deuterium sources and amines as organocatalysts. The deuteration strategy is scalable and works on enals with a variety of substituted arene or heterocycle motifs as well as enones. The method has been applied to the synthesis of deuterated drug precursors.
New synthetic route to N,N-disubstituted 3-aryl-3-pyridylpropylamines: Pheniramines from 3-aryl-3-(2-pyridyl)propanals
Marchetti, Mauro,Sechi, Barbara,Azzena, Ugo,Botteghi, Carlo,Paganelli, Stefano,Ponte, Gino Del,Stefani, Helio A.
, p. 219 - 225 (2007/10/03)
3-Aryl-3-(2-pyridyl)propanals 3, useful precursors compound for the H1 antihistaminic agents Pheniramines 1 were prepared following three different reaction pathways: the first one involves the rhodium catalyzed regiospecific hydroformylation of cinnamaldehyde acetals 4; the second one was carried out through the hydro-hydroxyacetamidation reaction on 1-aryl-1-(2-pyridyl)ethenes 2 followed by oxidative cleavage of the intermediate α-hydroxybutanamides 10; the third one was accomplished through alkylation of 2-benzylpyridines 12 with 2-bromomethyl-1,3-dioxolane 13 using LDA as deprotonating agent. The last preparative route showed to be the most convenient giving Pheniramine 1 up to 80 percent overall yield.
