- Iron-catalyzed Minisci acylation of N-heteroarenes with α-keto acids
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An efficient and mild protocol has been developed for the Minisci acylation reactions of nitrogen-containing heteroarenes with α-keto acids. Distinct from the conventional Minisci acylation conditions, the chemistry was performed using non-noble metal Fe(II), instead of expensive Ag(I) salt, as catalyst. A wide range of substrates, including aliphatic or aromatic α-keto acids, as well as various N-heteroarenes, proved to be compatible with the protocol. Scale-up experiment also demonstrates the practicality of the approach.
- Wang, Xiu-Zhi,Zeng, Cheng-Chu
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p. 1425 - 1430
(2019/02/01)
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- Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen
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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.
- Sterckx, Hans,De Houwer, Johan,Mensch, Carl,Herrebout, Wouter,Tehrani, Kourosch Abbaspour,Maes, Bert U.W.
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supporting information
p. 144 - 153
(2016/04/05)
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- Analogues of fenarimol are potent inhibitors of trypanosoma cruzi and are efficacious in a murine model of chagas disease
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We report the discovery of nontoxic fungicide fenarimol (1) as an inhibitor of Trypanosoma cruzi (T. cruzi), the causative agent of Chagas disease, and the results of structure-activity investigations leading to potent analogues with low nM IC50s in a T. cruzi whole cell in vitro assay. Lead compounds suppressed blood parasitemia to virtually undetectable levels after once daily oral dosing in mouse models of T. cruzi infection. Compounds are chemically tractable, allowing rapid optimization of target biological activity and drug characteristics. Chemical and biological studies undertaken in the development of the fenarimol series toward the goal of delivering a new drug candidate for Chagas disease are reported.
- Keenan, Martine,Abbott, Michael J.,Alexander, Paul W.,Armstrong, Tanya,Best, Wayne M.,Berven, Bradley,Botero, Adriana,Chaplin, Jason H.,Charman, Susan A.,Chatelain, Eric,Von Geldern, Thomas W.,Kerfoot, Maria,Khong, Andrea,Nguyen, Tien,McManus, Joshua D.,Morizzi, Julia,Ryan, Eileen,Scandale, Ivan,Thompson, R. Andrew,Wang, Sen Z.,White, Karen L.
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supporting information; experimental part
p. 4189 - 4204
(2012/07/27)
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- A New, Convenient Synthesis of Monoaroylpyrazines via Homolytic Substitution
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Reactions of 2-pyrazinecarboxylic acid (1) with aroyl radicals to give 5-aroyl-2-pyrazinecarboxylic acids 3 followed by decarboxylation provide convenient access to aryl 2-pyrazinyl ketones (2-aroylpyrazines) 4.
- Heinisch, G.,Loetsch, G.
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p. 119 - 121
(2007/10/02)
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