68043-60-7Relevant academic research and scientific papers
Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen
Sterckx, Hans,De Houwer, Johan,Mensch, Carl,Herrebout, Wouter,Tehrani, Kourosch Abbaspour,Maes, Bert U.W.
supporting information, p. 144 - 153 (2016/04/05)
The methylene group of various substituted 2- and 4-benzylpyridines, benzyldiazines and benzyl(iso)quinolines was successfully oxidized to the corresponding benzylic ketones using a copper or iron catalyst and molecular oxygen as the stoichiometric oxidant. Application of the protocol in API synthesis is exemplified by the alternative synthesis of a precursor to the antimalarial drug Mefloquine. The oxidation method can also be used to prepare metabolites of APIs which is illustrated for the natural product papaverine. ICP-MS analysis of the purified reaction products revealed that the base metal impurity was well below the regulatory limit.
Synthesis of Azaanthraquinones: Homolytic Substitution of Pyridines
Cameron, Donald W.,Deutscher, Kenneth R.,Feutrill, Geoffrey I.,Hunt, Dianne E.
, p. 1451 - 1468 (2007/10/02)
Synthesis of specific di- and tri-hydroxyazaanthraquinones by Friedel-Crafts procedures is limited by orientational ambiguity and by the lack of reactivity of pyridine derivatives in electrophilic acylation processes; however, suitable pyridines have been made to undergo radical benzoylation and benzylation at unsubstituted positions 2, 4 and 6.In particular, derivatives of pyridine-3-carbonitrile have been benzoylated at positions 2 and 4.Ring closure by intramolecular Houben-Hoesch reaction has then led to specifically substituted 1- and 2-azaanthraquinones and thence to the antibiotic bostrycoidin (1).
