105-36-2Relevant articles and documents
In situ generation of nitrile oxides from copper carbene and tert -butyl nitrite: Synthesis of fully substituted isoxazoles
Chen, Rongxiang,Ogunlana, Abosede Adejoke,Fang, Shangwen,Long, Wenhao,Sun, Hongmei,Bao, Xiaoguang,Wan, Xiaobing
, p. 4683 - 4687 (2018)
Herein, we present a novel [3 + 2] cycloaddition reaction of β-keto esters with nitrile oxides, which were generated in situ from copper carbene and tert-butyl nitrite. This three-component reaction provides new methodology for the direct synthesis of fully substituted isoxazole derivatives, featuring mild reaction conditions, readily accessible starting materials and simple operation. The experimental studies and DFT calculations suggest that the reaction starts with the generation of the key intermediate nitrile oxides, followed by a [3 + 2] cycloaddition reaction of β-keto esters to give the final isoxazole products.
Activation of alkyl halides via a silver-catalyzed carbene insertion process
Dias, H. V. Rasika,Browning, R. Greg,Polach, Sharon A.,Diyabalanage, Himashinie V. K.,Lovely, Carl J.
, p. 9270 - 9271 (2003)
The silver complex [HB(3,5-(CF3)2Pz)3]Ag(THF) featuring a highly fluorinated tris(pyrazolyl)borate ligand catalyzes the formation of aliphatic carbon-halogen bond activation products under remarkably mild conditions. For example, the reaction between CHCl3 and ethyl diazoacetate (EDA) at room temperature in the presence of the silver catalyst afforded HClC(CO2Et)CCl2H in 60% yield. The presence of β-hydrogens on the alkyl halide leads to net hydrogen halide addition to the carbene and an alkene. Copyright
Visible-Light-Assisted Gold-Catalyzed Fluoroarylation of Allenoates
Feng, Chao,Tang, Hai-Jun,Zhang, Xinggui,Zhang, Yu-Feng
, p. 5242 - 5247 (2020)
A strategically novel synthetic method for the fluoroarylation of allenic ester was developed that enables the expedient construction of a host of β-fluoroalkyl-containing cinnamate derivatives. The reaction proceeds through visible-light-promoted gold redox catalysis, occurs smoothly under very mild reaction conditions, accommodates a large variety of functional groups, and more importantly allows the incorporation of fluorine and aryl groups with excellent regio- and stereoselectivity. The concomitant activation mode for both the allene motif and the hydrogen fluoride is key for the success of the reaction.
Facile One Pot Multi-Component Solvent-Free Synthesis of 2,4,5-Trisubstituted Imidazoles Using “Green” and Expeditious Ionic Liquid Catalyst under Microwave Irradiation
Sonyanaik,Ashok,Rambabu,Ravi,Kurumanna,Madhu,Sakram
, p. 537 - 540 (2018)
Acetic acid functionalized poly(4-vinylpyridinium) bromide is a highly efficient and recyclable catalyst for the construction of 2,4,5-trisubstituted imidazole derivatives by a three-component condensation of benzyl with various aldehydes and ammonium acetate under solvent free conditions. The microwave initiated process leads to analytically pure compounds within 2–5 min. The advantages of this “green” methodology are cost-effectiveness, simple procedure, low energy consumption, no involvement of organic solvents, safe operation, clean reaction profile, high yields, and recyclability of the catalyst.
REACTION OF ETHYL TRIBUTYLSTANNYLACETATE WITH CARBONYL COMPOUNDS IN THE PRESENCE OF TRIBUTYLSTANNIC IODIDE
Kashin, A. N.,Tul'chinskii, M. L.,Beletskaya, I. P.,Reutov, O. A.
, p. 1937 (1982)
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Synthesis process of thiazole medical intermediate
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Paragraph 0013, (2021/06/09)
The invention discloses a synthesis process of thiazole medical intermediate.The synthesis process comprises the following steps: step 1, mixing ethyl pyruvate and dichloromethane of which the volume is 2 times that of the ethyl pyruvate at room temperature, adding an obtained mixture into a reactor, starting stirring, and keeping the temperature of a system at about 20 DEG C; step 2, starting to dropwise add a dichloromethane solution of bromine, controlling the temperature to enable the system to be about 20-30 DEG C, sealing the reactor, and introducing a strong alkali solution to absorb acid gas HBr; and step 3, after dropwise adding is completed, closing a cold well, performing stirring at normal temperature for about 2 hours until the color of the reaction liquid gradually becomes light yellow to light brown, monitoring that no raw material exists through TLC, and concentrating the obtained reaction liquid. According to the synthesis process of the thiazole medical intermediate, by introducing the defoaming agent n-hexane, generated gas foam can be quickly dissolved out and released from the solvent, and the phenomenon of one-time flushing is avoided; and by introducing the n-hexane solvent, solids can be effectively separated out at low temperature, the impurity content can be controlled to be about 1%, the purification difficulty is greatly reduced, and crystallization is facilitated.
Synthesis, antiinflammatory activity, and molecular docking studies of bisphosphonic esters as potential MMP-8 and MMP-9 inhibitors
Cortes-Pacheco, Abimelek,Jiménez-Arellanes, María Adelina,Juárez-Vázquez, María del Carmen,López-Torres, Adolfo,Palacios-Can, Francisco José,Ramírez-Marroquín, Oscar Abelardo,Razo-Hernández, Rodrigo Said,Valcarcel-Gami?o, José Antonio
supporting information, p. 1277 - 1287 (2020/07/10)
Bisphosphonic acids (or bisphosphonates) have been successfully used in the clinic treatment of bone diseases for over decades. Additionally, the antiinflammatory activity of these compounds has been gaining attention. In our previous work, we synthesized and in vivo evaluated the bisphosphonic esters 1 and 2, finding a moderate edema inhibition upon oral and topical administration on BALB/c mice. Thus, in this work, the bioisosteric replacement of an amide functional group for an ester afforded the new bisphosphonates 3–6, which had a moderate oral edema inhibition (25 mg/kg dose) and a significant topical antiinflammatory activity (2 mg/ear) on BALB/c mice, with 6 being the most active hit (55.9% edema inhibition), comparable to the positive control (55.5% edema inhibition) on a TPA topical model. Next, to assess the acute toxicity of the synthesized derivatives, test animals were administered with 50–100 mg/kg of 3–6, respectively, by an oral route, and after 14 days, neither lethality nor a significative weight loss were observed. Finally, a structure–activity relationship (SAR) and a molecular docking analysis of 3–6 helped us to explain the trend observed in biological tests. Considering all these aspects, we propose the inhibition of MMP-8 and MMP-9 as a possible action mechanism of the synthesized derivatives.