34451-66-6Relevant articles and documents
Catalytic Transfer Hydration of Cyanohydrins to α-Hydroxyamides
Kanda, Tomoya,Naraoka, Asuka,Naka, Hiroshi
supporting information, p. 825 - 830 (2019/01/14)
We report the palladium(II)-catalyzed transfer hydration of cyanohydrins to α-hydroxyamides by using carboxamides as water donors. This method enables selective hydration of various aldehyde- and ketone-derived cyanohydrins to afford α-mono- and α,α-disubstituted-α-hydroxyamides, respectively, under mild conditions (50 °C, 10 min). The direct conversion of fenofibrate, a drug bearing a benzophenone moiety, into a functionalized α,α-diaryl-α-hydroxyamide was achieved by means of a hydrocyanation-transfer hydration sequence. Preliminary kinetic studies and the synthesis of a site-specifically 18O-labeled α-hydroxyamide demonstrated the carbonyl oxygen transfer from the carboxamide reagent into the α-hydroxyamide product.
4-Benzyloxy-γ-sultone derivatives: Discovery of a novel family of non-nucleoside inhibitors of human cytomegalovirus and varicella zoster virus
De Castro, Sonia,García-Aparicio, Carlos,Andrei, Graciela,Snoeck, Robert,Balzarini, Jan,Camarasa, María-José,Velázquez, Sonsoles
experimental part, p. 1582 - 1591 (2010/01/07)
We report the synthesis and antiviral activity of a new family of non-nucleoside antivirals, derived from the 4-keto-1,2-oxathiole-2,2-dioxide (β-keto-γ-sultone) heterocyclic system. Several 4- and 5-substituted-5H-1,2-oxathiole-2,2-dioxide derivatives were found to have a selective inhibitory activity against human cytomegalovirus (HCMV) and varicella zoster virus (VZV) replication in vitro, being inactive against a variety of other DNA and RNA viruses. A structure-activity relationship (SAR) study showed that the presence of a benzyl at the 5 position and a benzyloxy substituent at the 4 position are a prerequisite for anti-HCMV and VZV activity. The novel compounds do not show cross-resistance against a wide variety of mutant drug-resistant HCMV strains, pointing to a novel mechanism of antiviral action.
Solvent-free synthesis of racemic α-aminonitriles
Baeza, Alejandro,Najera, Carmen,Sansano, Jose M.
, p. 1230 - 1234 (2008/02/02)
A very simple one-step, environmentally friendly procedure for the synthesis of α-aminonitriles from aldehydes and ketones, using trimethylsilyl cyanide in the absence of solvent, is reported. The active catalyst of this three-component (Strecker) reaction was the amine employed in the transformation. In general, aldehydes react more rapidly than ketones and give almost quantitative yields of the corresponding α-aminonitriles in less than fifteen minutes. However, only cyclic ketones afford the corresponding α-aminonitriles in excellent chemical yields under these conditions. Georg Thieme Verlag Stuttgart.
