- Tandem Pd-catalyzed C-C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes
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The first successful synthesis of 1H-2,3-benzoxazine 3-oxides has been described. The efficiency of the approach is provided by the C-C-coupling of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitroalkanes catalyzed by Pd(dba)2/JohnPhos system followed by in situ recyclization of the intermediates. Several representative transformations allowing selective modification of the nitronate as well as malonate functionalities in the resulting compounds are demonstrated.
- Mikhaylov, Andrey A.,Dilman, Alexander D.,Novikov, Roman A.,Khoroshutina, Yulia A.,Struchkova, Marina I.,Arkhipov, Dmitry E.,Nelyubina, Yulia V.,Tabolin, Andrey A.,Ioffe, Sema L.
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- ARYL AMIDE KINASE INHIBITORS
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The present disclosure is generally directed to compounds which can inhibit AAK1 (adaptor associated kinase 1), compositions comprising such compounds, and methods for inhibiting AAK1.
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Page/Page column 75; 76
(2015/02/02)
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- General synthetic strategies towards N-alkyl sulfoximine building blocks for medicinal chemistry and the use of dimethylsulfoximine as a versatile precursor
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The sulfoximine group has great potential as a substituent in drug discovery, as evidenced by two new clinical candidates, and can be viewed as an isosteric alternative to the commonly used sulfone. Our aim was to improve the accessibility of this group by synthesising a diverse range of S-alkyl and N-alkyl sulfoximine building blocks with procedures that are applicable on a practical scale (>10 g). In particular, synthesis of the less well exploited N-alkyl sulfoximines and the use of dimethylsulfoximine as a versatile, commercially available precursor is discussed.
- Goldberg, Frederick W.,Kettle, Jason G.,Xiong, Jian,Lin, Daoguang
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p. 6613 - 6622
(2015/03/30)
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- Versatile synthesis of isoquinolines and isochromenes by Pd-catalyzed oxidative carbonylation of (2-alkynyl)benzylideneamine derivatives
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Isoquinoline-4-carboxylic esters 3 and isochromene-4-carboxylic esters 4 have been conveniently prepared by direct PdI2-catalyzed oxidative heterocyclization/alkoxycarbonylation of readily available (2- alkynylbenzylidene)amine derivatives. In particular, (2-alkynylbenzylidene) (tert-butyl)amines 2 selectively afforded isoquinoline derivatives 3 by N-cyclization, whereas N-(2-alkynylbenzylidene)-N′-phenylhydrazines 5 led to the formation of isochromenes 4 through O-cyclization ensuing from water attack on the imino group of the substrate. Reactions were carried out in alcoholic solvents at 80-100 °C and under 20-80 atm (at 25 °C) of a 4:1 mixture of CO/air, in the presence of PdI2 (2-10 mol-%) in conjunction with KI (KI/PdI2 molar ratio = 10). In the case of imines 2, the use of a dehydration agent, such as trialkyl orthoformate, was necessary to obtain satisfactory yields of isoquinolines 3.
- Gabriele, Bartolo,Veltri, Lucia,Maltese, Vito,Spina, Rosella,Mancuso, Raffaella,Salerno, Giuseppe
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p. 5626 - 5635
(2011/11/29)
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- Inter- and intramolecular hydroacylation of alkenes employing a bifunctional catalyst system
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Based on a conceptually innovative bifunctional P,N ligand, an efficient protocol for the rhodium-catalyzed inter- and intramolecular hydroacylation of alkenes has been developed.
- Vautravers, Nicolas R.,Regent, Damien D.,Breit, Bernhard
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p. 6635 - 6637
(2011/06/27)
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- Inhibitors of inosine monophosphate dehydrogenase: SARs about the N-[3-methoxy-4-(5-oxazolyl)phenyl moiety
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The first reported structure-activity relationships (SARs) about the N-[3-methoxy-4-(5-oxazolyl)phenyl moiety for a series of recently disclosed inosine monophosphate dehydrogenase (IMPDH) inhibitors are described. The syntheses and in vitro inhibitory values for IMPDH II, and T-cell proliferation (for select analogues) are given.
- Iwanowicz, Edwin J.,Watterson, Scott H.,Guo, Junqing,Pitts, William J.,Murali Dhar,Shen, Zhongqi,Chen, Ping,Gu, Henry H.,Fleener, Catherine A.,Rouleau, Katherine A.,Cheney, Daniel L.,Townsend, Robert M.,Hollenbaugh, Diane L.
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p. 2059 - 2063
(2007/10/03)
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- Novel diamide-based inhibitors of IMPDH
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A series of novel amide-based small molecule inhibitors of inosine monophosphate dehydrogenase is described. The synthesis and the structure-activity relationships (SARs) derived from in vitro studies are presented.
- Gu, Henry H.,Iwanowicz, Edwin J.,Guo, Junqing,Watterson, Scott H.,Shen, Zhongqi,Pitts, William J.,Dhar,Fleener, Catherine A.,Rouleau, Katherine,Sherbina,Witmer, Mark,Tredup, Jeffrey,Hollenbaugh, Diane
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p. 1323 - 1326
(2007/10/03)
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