- Base-controlled product switch in the ruthenium-catalyzed protodecarbonylation of phthalimides: A mechanistic study
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The whole reaction mechanism of the ruthenium-catalyzed protodecarbonylation of N-substituted phthalimides into secondary amides was unravelled by a combined experimental and theoretical study. The chemoselectivity of the reaction, which is catalyzed by para-cymene coordinated Ru(ii) species all over the catalytic cycle, is exclusively controlled by the unique roles of the bases. Meanwhile, in the presence of K2CO3 or KOH at high temperatures, the same product (benzamide) is mainly formed, whereas at low temperatures, KOH led to an unexpected side-product (phthalamic acid) and no reactivity was observed with K2CO3. The non-covalent interactions between the potassium cations and the different carbonyl groups in the molecules are key to providing a thermodynamically favourable pathway with energetically accessible transition states. The unexpected formation of carbon dioxide (CO2) in the course of the reaction originates from the phthalimide substrate and the base K2CO3 in two different elementary steps, respectively.
- D'Alterio, Massimo Christian,Yuan, Yu-Chao,Bruneau, Christian,Talarico, Giovanni,Gramage-Doria, Rafael,Poater, Albert
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p. 180 - 186
(2020/01/13)
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- Rivaroxaban impurity reference substance and preparation method thereof
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The invention discloses a rivaroxaban impurity reference substance. The full name of the impurity reference substance is (S)-N-methyl-N-((2-oxa-3-(4-(3-oxomorpholino)phenyl)-5-oxazolidinyl)methyl)phthalamide. The invention also discloses a synthesis method of the impurity reference substance, and the method comprises the following steps: reacting phthalic anhydride with a methylamine aqueoussolution to generate 2-(methylaminoformyl)benzoic acid, and then reacting the 2-(methylaminoformyl)benzoic acid with the rivaroxaban intermediate RVXB-3 through a coupling agent under the action of solid alkali to obtain the target rivaroxaban impurity reference substance. The rivaroxaban impurity is simple in preparation process and high in purity, and a qualified rivaroxaban impurity referencesubstance can be provided for quality control of rivaroxaban.
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Paragraph 0024-0054
(2020/07/12)
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- Compounds and methods for inducing chondrogenesis
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The present invention provides compounds and compositions for the amelioration of arthritis and joint injuries by inducing mesenchymal stem cells into chondrocytes.
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Page/Page column 38; 85; 86
(2016/10/31)
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- Phthalimidomethyl as a drug pro-moiety. Probing its reactivity
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Phthalimidomethyl derivatives 1, encompassing a wide range of leaving group abilities, are rapidly hydrolysed to the corresponding phthalamic acid via rate-determining attack at the phthalimide carbonyl group.
- Iley, Jim,Calheiros, Teresa,Moreira, Rui
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p. 955 - 958
(2007/10/03)
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- A convenient method of N-methylphthalimide synthesis
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We suggest a convenient method to obtain N-methylphthalimide with a high yield in the reaction of phthalic anhydride with aqueous methylamine.
- Vasilevskaya,Yakovleva,Kobrin
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p. 2463 - 2465
(2007/10/02)
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- 11a-Methano-TXA compounds
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The present invention provides novel 11a-methano-TXA compounds and intermediates and processs for their preparation. Further provided are methods for using these novel TXA analogs as inhibitors of thromboxane synthetase, rendering these analogs useful for a variety of pharmacological purposes. These pharmacological uses include anti-inflammatory, anti-thromobitc, and anti-asthma indications.
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