- Access to Stable Quaternary Phosphiranium Salts by P-Alkylation and P-Arylation of Phosphiranes
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We report the preparation of phosphiranium salts by quaternarization of phosphiranes, a class of sensitive, highly strained, and poorly nucleophilic cyclic phosphines. High-yielding introduction of a varied set of alkyl groups including methylene ester ar
- Alayrac, Carole,Botella, Clément,Comesse, Sébastien,Dalla, Vincent,Gasnot, Julien,Gaumont, Annie-Claude,Lakhdar, Sami,Taillier, Catherine
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supporting information
p. 883 - 888
(2020/05/28)
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- HERBICIDAL COMPOUNDS
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The present invention relates to herbicidally active thiadiazole derivatives, as well as to processes and intermediates used for the preparation of such derivatives. The invention further extends to herbicidal compositions comprising such derivatives, as well as to the use of such compounds and compositions in controlling undesirable plant growth: in particular the use in controlling weeds, in crops of useful plants.
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Page/Page column 43-44
(2020/06/05)
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- Regioselectivity of thiouracil alkylation: Application to optimization of Darapladib synthesis
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Darapladib is one of the most potent Lp-PLA2 (Lipoprotein-associated phospholipase A2) inhibitor with an IC50 of 0.25 nM. We demonstrate that a crucial step of Darapladib synthesis was not correctly described in the litera
- Guibbal, Florian,Bénard, Sébastien,Patché, Jessica,Meneyrol, Vincent,Couprie, Jo?l,Yong-Sang, Jennyfer,Meilhac, Olivier,Jestin, Emmanuelle
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supporting information
p. 787 - 792
(2018/01/17)
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- Dehydration-type Ti-Claisen Condensation (Carbonhomologation) of α-Heteroatom-substituted Acetates with Alkyl Formates: Utilization as (Z)-Stereodefined Cross-coupling Partners and Application to Concise Synthesis of Strobilurin A
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TiCl4?Et3N or ?Bu3N reagent conducted a highly (Z)-stereoselective carbon homologation (dehydration type Ti-Claisen condensation) of alkyl α-heteroatom (halo and sulfonyloxy)-substituted acetates (XCH2CO2R) with alkyl formates (HCO2R) to afford various alkyl β-alkoxy-α-halo or sulfonyloxy-substituted acrylates (24 examples; 51%–91% yield). Stereoretentive Suzuki-Miyaura, Negishi, and Sonogashira cross-couplings using the obtained methyl β-methoxy-α-halo or sulfonyloxy-substituted acrylates proceeded smoothly to produce a variety of β-alkoxy-α-substituted acrylates in moderate to high yield (35 examples; 29%–99% yield). As a successful application, a 3-step straightforward synthesis of strobilurin A was performed utilizing the present reaction sequence (dehydration type Ti-Claisen condensation and Suzuki-Miyaura cross-coupling), wherein the geometry of the three consecutive olefins (2E,3Z,5E) was completely maintained. (Figure presented.).
- Nakatsuji, Hidefumi,Kamada, Risa,Kitaguchi, Hideya,Tanabe, Yoo
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p. 3865 - 3879
(2017/11/15)
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- Reactions of diazo esters with electron-deficient alkenes in the presence of Lewis acids
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1,3-Dipolar cycloaddition reaction of diazo esters to electron-deficient dipolarophiles to yield the corresponding 1- or 2-pyrazolines was found to be significantly accelerated with Lewis acids (Yb(OTf)3, Sc(OTf) 3, GaCl3, EtAlCl2). The use of GaCl3 as the catalyst leads to the acceleration not only of the 1,3-dipolar cycloaddition reaction, but also subsequent insertion of the CHCO2Me electrophilic fragment of methyl diazoacetate into the N-H bond of 2-pyrazolines formed. Such Lewis acids as SnCl4, BF3, TiCl4, and In(OTf)3 are not efficient in the described processes, since they rapidly decompose starting diazo compounds.
- Novikov,Platonov,Dokichev,Tomilov,Nefedov
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experimental part
p. 984 - 990
(2011/02/27)
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- Synthesis, characterization and solubility studies of four new highly water soluble 1,3,5-triaza-7-phosphaadamantane (PTA) salts and their gold(I) complexes
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The synthesis of new water soluble N-alkylated derivatives of 1,3,5-triaza-7-phosphaadamantane is presented. The compounds were characterized by means of NMR and IR spectroscopy, mass spectrometry, high resolution mass spectrometry, elemental analysis and
- Sch?fer, Sascha,Frey, Wolfgang,Hashmi, A. Stephen K.,Cmrecki, Vesna,Luquin, Asunción,Laguna, Mariano
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experimental part
p. 1925 - 1932
(2010/08/21)
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- ENDOTHELIN RECEPTOR ANTAGONISTS
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The present invention relates to dihydroisoindole compounds, pharmaceutical compositions containing these compounds, and their use as endothelin receptor antagonists.
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