762-42-5Relevant articles and documents
Thiol-yne click reaction: an interesting way to derive thiol-provided catechols
Nador, Fabiana,Mancebo-Aracil, Juan,Zanotto, Duham,Ruiz-Molina, Daniel,Radivoy, Gabriel
, p. 2074 - 2082 (2021/01/29)
The hydrothiolation of activated alkynes is presented as an attractive and powerful way to functionalize thiols bearing catechols. The reaction was promoted by a heterogeneous catalyst composed of copper nanoparticles supported on TiO2 (CuNPs/TiO2) in 1,2-dichloroethane (1,2-DCE) under heating at 80 °C. The catalyst could be recovered and reused in three consecutive cycles, showing a slight decrease in its catalytic activity. Thiol derivatives bearing catechol moieties, obtained through a versatile Michael addition, were reacted with different activated alkynes, such as methyl propiolate, propiolic acid, propiolamide or 2-ethynylpyridine. The reaction was shown to be regio- and stereoselective towards anti-Markovnikov Z-vinyl sulfide in most cases studied. Finally, some catechol derivatives obtained were tested as ligands in the preparation of coordination polymer nanoparticles (CNPs), by taking the advantage of their different coordination sites with metals such as iron and cobalt.
Synthesis of dimethyl acetylenedicarboxylate
-
Paragraph 0013-0014; 0016; 0020; 0024, (2018/10/11)
The invention discloses synthesis of dimethyl acetylenedicarboxylate. The synthesis steps comprise: (1) dissolving 2,3-dibromosuccinic acid in methanol, adding concentrated sulfuric acid to the reaction solution in a dropwise manner, continuously stirring, and carrying out a reaction for 2-3 h to obtain 2,3-methyl dibromosuccinate; and (2) dissolving the 2,3-methyl dibromosuccinate obtained in thestep (1) into ethanol, adding an alkali substance, stirring, carrying out a heating reflux reaction, and carrying out post-treatment to obtain dimethyl acetylenedicarboxylate. According to the present invention, the operation is simple, the requirement on the operation technology of the technician is not high, the production cost can be effectively saved, and the dimethyl acetylenedicarboxylate obtained through the method has the high purity and can be directly used for the next reaction.
A 2- fluoro fumaric acid ester (formula I) and its preparation method and application
-
Paragraph 0059, (2017/01/23)
The invention discloses 2-fuloro fumarate (formula I) and a preparation method thereof. Experiments show that: the kinds of compounds are capable of effectively inhibiting NF-kB transcriptional activity introduced by TNF-alpha, and further are capable of treating diseases introduced by NF-kB, such as psoriasis, multiple sclerosis, arthritis, eye inflammation or allergy, asthma and lupus erythematosus, and can be used as an immunosuppressant for organ transplantation.
Mechanism and scope of the base-induced dehalogenation of (E)-diiodoalkenes
Resch, Daniel,Lee, Chang Heon,Tan, Siew Yoong,Luo, Liang,Goroff, Nancy S.
, p. 730 - 737 (2015/01/30)
A wide range of nucleophiles have induced the elimination of iodine from (E)-diiodoalkenes to form alkynes under surprisingly mild conditions. The iodide anion is particularly efficient, and can drive the reaction to completion in less than 1 hour at room temperature in a polar aprotic solvent. Detailed investigations have suggested the reaction has a bimolecular polar mechanism. The deiodination reaction can be driven to completion with 1 equiv. of nucleophile and is partially catalytic with substoichiometric amounts of deiodinating reagent. Kinetic analysis of the stoichiometric iodide-induced reaction indicated an overall pseudo-first-order behavior. The reaction exhibited strong solvent effects, with much slower reactions observed in protic solvents than in polar aprotic solvents. The substrate dimethyl (2E)-2,3-diiodo-butene-2-dioate demonstrated orthogonal reactivity for either elimination or hydrolysis, depending on the solvent and nucleophile used. This reaction is a major pathway for all the diiodoalkenes examined, and represents a challenge and an opportunity for using these substrates in organic synthesis.
PREPARATION OF ORGANOSILICON-CONTAINING TRIAZOLES
-
, (2011/04/19)
The disclosure includes methods for preparing organosilicon-containing 1,2,3-triazoles by reacting an organosilicon containing azide with an alkyne compound or an organosilicon containing alkyne with an azide compound under thermal reaction conditions.
Synthesis and transformations of 5-substituted 2-aryl-7H-[1,2,4]triazolo[3, 2-b][1,3]thiazin-7-ones and 2-aryl-2,3-dihydro-4H-[1,3]thiazino[3,2-a] benzimidazol-4-ones
Britsun,Esipenko,Chernega,Lozinskii
, p. 108 - 113 (2007/10/03)
3-Aryl-1,2,4-triazole-5-thiones react with dimethyl acetylenedicarboxylate and methyl 3-phenyl-propynoate to afford the corresponding 5-substituted 2-aryl-7H-[1,2,4]triazolo[3,2-b][1,3]thiazin-7-ones. Treatment of 2-aryl-2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-ones with alkalies leads to formation of 3-(benzimidazol-2-ylsulfanyl)-3-arylpropionic acids, their reaction with methyl p-toluenesulfonate yields 1-(3-methyl-2-thioxo-2,3- dihydro-1N-benzimidazol-1-yl)-3-phenyl-2-propen-1-one, and oxidation with hydrogen peroxide gives benzimidazole-2-sulfonic acid and 3-aryl-2-propenoic acids. 2005 Pleiades Publishing, Inc.
7-oxabicyclo[2.2.1]heptadiene derivatives: Reactivity towards Bronsted acids
Maggiani, Alain,Tubul, Arlette,Brun, Pierre
, p. 2495 - 2496 (2007/10/03)
7-Oxabicyclo[2.2.1]heptadiene derivatives can be converted to phenols, fulvenes and/or the products from a retro-Diels-Alder-like reaction by treatment with Bronsted acids; the outcome of the reaction depends on the experimental conditions and the nature of the Bronsted acid used.
Reductive dehalogenation of aliphatic vic-dihalides with metallic samarium in a methanolic medium
Yanada, Reiko,Negoro, Nobuyuki,Yanada, Kazuo,Fujita, Tetsuro
, p. 9313 - 9316 (2007/10/03)
In the title reaction, eight vic-dibromides and three vinylene dibromides gave the corresponding debromination products (alkenes and alkynes) at room temperature under neutral condition and an argon atmosphere. 2,3-Dibromosuccinic acid derivatives gave overreduction products or an unusual coupling dimer.
Barrelene Derivatives-Potential Modules for Assembly
Beerly, Rene,Rebek, Julius
, p. 1813 - 1816 (2007/10/02)
Dihydrobarrelene tetraamide 8 was prepared by Diels-Alder reaction of 4 and 5 and indirect transformation of the ester into amide groups.The crystal structure of 8 showed an unpredicted conformation of the four amide groups.
