- 2,2,2-Trifluoroethyl Oxalates in the One-Pot Parallel Synthesis of Hindered Aliphatic Oxamides
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A simple parallel synthesis approach to unsymmetrical N1,N2-substituted aliphatic oxamides using methyl (2,2,2-trifluoroethyl) oxalate and bis(2,2,2-trifluoroethyl) oxalate was developed. The method was validated on a 52-membered set of the oxamides, derived mainly from hindered primary and secondary aliphatic amines, and gave the products with a high overall success rate in moderate yields.
- Bogolubsky, Andrey V.,Moroz, Yurii S.,Mykhailiuk, Pavel K.,Pipko, Sergey E.,Grishchenko, Alexander V.,Zhemera, Anton V.,Konovets, Anzhelika I.,Doroschuk, Roman A.,Dmytriv, Yurii V.,Zaporozhets, Olga A.,Tolmachev, Andrey
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- Dual Hypervalent Iodine(III) Reagents and Photoredox Catalysis Enable Decarboxylative Ynonylation under Mild Conditions
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A combination of hypervalent iodine(III) reagents (HIR) and photoredox catalysis with visible light has enabled chemoselective decarboxylative ynonylation to construct ynones, ynamides, and ynoates. This ynonylation occurs effectively under mild reaction conditions at room temperature and on substrates with various sensitive and reactive functional groups. The reaction represents the first HIR/photoredox dual catalysis to form acyl radicals from α-ketoacids, followed by an unprecedented acyl radical addition to HIR-bound alkynes. Its efficient construction of an mGlu5 receptor inhibitor under neutral aqueous conditions suggests future visible-light-induced biological applications.
- Huang, Hanchu,Zhang, Guojin,Chen, Yiyun
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supporting information
p. 7872 - 7876
(2015/06/30)
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- Pd/C-catalyzed synthesis of oxamates by oxidative cross double carbonylation of amines and alcohols under Co-catalyst, base, dehydrating agent, and ligand-free conditions
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This work reports a mild, efficient, and ligand-free Pd/C-catalyzed protocol for the oxidative cross double carbonylation of amines and alcohols. Notably, the reaction does not requires any base, co-catalyst, dehydrating agent, or ligand. Pd/C solves the problem of catalyst recovery, and the catalyst was recycled up to six times.
- Gadge, Sandip T.,Bhanage, Bhalchandra M.
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p. 6793 - 6797
(2013/07/26)
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- SUBSTITUTED TRIAZOLES AS ANGIOTENSIN II ANTAGONISTS
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Novel substituted triazoles of the formula (I), which are useful as angiotensin II antagonists, are disclosed. STR1
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- Nonpeptide angiotensin II antagonists derived from 4H-1,2,4-triazoles and 3H-imidazo[1,2-b][1,2,4]triazoles
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By a variety of synthetic routes, we have synthesized a series of 3,4,5- trisubstituted 4H-1,2,4-triazoles and a related series of 3H-imidazo[1,2- b][1,2,4]triazoles and evaluated them in vitro and in vivo as angiotensin II (AII) antagonists. Principal efforts focused on triazoles bearing an n-alkyl substituent at C3 and a 4-[(2-carboxybenzoyl)amino]benzyl, (2'- carboxybiphenyl-4-yl)methyl, or [2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl side chain at N4. Among numerous variations at C5, benzylthio groups gave the best potency. Particularly noteworthy was 3-n-butyl-5-[(2- carboxybenzyl)thio]-4-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-4H-1,2,4- triazole (71, IC50 1.4 nM), which blocked the AII pressor response in conscious rats at 0.3 mg/kg iv with a duration of action of approximately 6 h, similar to that of DuP 753. Although 71 was active orally only at a 10- fold higher dose level, good oral bioavailability was demonstrated for a monoacidic analogue 62. Most potent among the bicyclic derivatives was 2-n- butyl-5,6-dimethyl-3-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-3H- imidazo[1,2-b][1,2,4]triazole (93, IC50 7.8 nM). The effects of hydrophobic, hydrogen-bonding, and ionic interactions with the AT1 receptor are considered.
- Ashton,Cantone,Chang,Hutchins,Strelitz,MacCoss,Chang,Lotti,Faust,Chen,Bunting,Schorn,Kivlighn,Siegl
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p. 591 - 609
(2007/10/02)
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- Effects of ethyl N-N-benzyl-methyl-oxamate in Meriones unguiculatus infected with Echinococcus multilocularis metacestodes. Biochemical and ultrastructural observations
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Ethyl N-N-benzyl-methyl-oxamate is a N-substituted derivative of the oxamic acid, well-known as inhibitor of the lactate dehydrogenase activity. The biochemical and ultrastructural effects of this drug in Echinococcus multilocularis metacestodes and the r
- Sarciron,Delabre-Defayolle,Audin,Petavy,Paris
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p. 607 - 610
(2007/10/02)
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