- Asymmetric Synthesis of Spiropyrazolones by Rhodium-Catalyzed C(sp2)?H Functionalization/Annulation Reactions
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Rhodium-catalyzed C(sp2)?H functionalization reactions of 4-aryl-5-pyrazolones followed by [3+2] annulation reactions with alkynes provide rapid access to highly enantioenriched five-membered-ring 4-spiro-5-pyrazolones. The use of a chiral SCpRh catalyst enabled the synthesis of a large range of spiropyrazolones with all-carbon quaternary stereogenic centers in up to 99 % yield and 98 % ee from readily available substrates.
- Zheng, Jun,Wang, Shao-Bo,Zheng, Chao,You, Shu-Li
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supporting information
p. 4540 - 4544
(2017/04/11)
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- Total synthesis of monocyclic pyrimidinium betaines with fatty alkyl chains
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Seven betaines were prepared by condensation of N,N'-diphenylamidines with malonic acid derivatives. The amidines were made via a multistep synthesis, starting from their corresponding fatty acids. Malonyl chloride and dipentachlorophenyl phenylmalonate, two derivatives of malonic acid, were obtained from malonic acid and benzyl chloride, respectively. Most of the products were characterized by IR, UV, 1H and 13C NMR. Biological assays of the synthesized betaines revealed their good antibacterial and antifungal activities against the Pseudomonas aeruginosa, Bacillus subtilis and Mucor ramannianus and an activity against Candida albicans.
- Malki, Fatiha,Touati, Abdelkader,Rahal, Said,Moulay, Saad
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p. 961 - 967
(2011/12/21)
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- Studies on non-thiazolidinedione antidiabetic agents. 1. Discovery of novel oxyiminoacetic acid derivatives
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A novel series of oxyiminoacetic acid derivatives were synthesized in an effort to develop a potent antidiabetic agent, which does not contain the 2,4-thiazolidinedione moiety. These compounds were evaluated for glucose and lipid lowering effects in genetically obese and diabetic KKAy mice. Several of the compounds showed strong antidiabetic activity, including functional potency at peroxisome proliferator-activated receptor (PPAR)-γ. (Z)-2-[4-[(5-Methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzyloxyimino]-2-(4- phenoxyphenyl)acetic acid (25) significantly reduced plasma glucose (33%, p0.01) and plasma triglycelide levels (43%, p0.01) even at a dosage of 0.001% in diet. Pharmacokinetic analyses of 25 are also reported.
- Imoto, Hiroshi,Imamiya, Eikoh,Momose, Yu,Sugiyama, Yasuo,Kimura, Hiroyuki,Sohda, Takashi
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p. 1349 - 1357
(2007/10/03)
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- Disposition of bornaprine hydrochloride in the rat. 1st Communication: Pharmacokinetic studies: Synthesis, plasma levels and elimination
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The biliary elimination and plasma concentration-time course of radioactivity and unchanged compound of 2-phenyl-bicyclo-[2.2.1]-heptane-2-carboxylic acid (4'-diethylaminopropyl)ester hydrochloride (bornaprine hydrochloride, Sormodren) were investigated a
- Neidlein,Pichler,Hege,Weymann
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p. 484 - 487
(2007/10/02)
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- Intramolecular Carbenoid Reactions of Pyrrole Derivatives. A Total Synthesis of (+/-)-Ipalbidine
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A mew method for alkaloid synthesis is described.The rhodium(II)-acetate-catalyzed decomposition of 3-(4-acetoxyphenyl)-1-diazo-4-(pyrrol-1-yl)-2-butanone (5d) gave 6-(4-acetoxyphenyl)-5,6-dihydro-7(8H)-indolizinone (6d) in 82percent yield via an intramolecular carbenoid reaction.The latter compound was converted in four steps in 13percent overall yield to (+/-)-ipalbidine (1b).
- Jefford, Charles W.,Kubota, Tadatoshi,Zaslona, Alexander
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p. 2048 - 2061
(2007/10/02)
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- COMPETITIVE INTRAMOLECULAR CARBENOID REACTIONS OF PYRROLE DERIVATIVES
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Rhodium(II) acetate-catalyzed decomposition of 1-diazo-3-phenyl-4-(pyrrol-1-yl)-butan-2-one and its p-methoxy derivative resulted in their intramolecular cyclization to form the 6-phenyl-5,6-dihydroindolizin-7(8H)-ones and 1-(pyrrol-1-yl)methylindan-3-ones as major and minor products respectively in high yields (77-89percent).The p-nitrophenyldiazo compound cyclized exclusively to the 5,6-dihydroindolizin-7(8H)-one in 76percent yield.
- Jefford, Charles W.,Zaslona, Alexander
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p. 6035 - 6038
(2007/10/02)
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