- Nickel-Catalyzed Cyanation of Aryl Thioethers
-
A nickel-catalyzed cyanation of aryl thioethers using Zn(CN)2 as a cyanide source has been developed to access functionalized aryl nitriles. The ligand dcype (1,2-bis(dicyclohexylphosphino)ethane) in combination with the base KOAc (potassium acetate) is essential for achieving this transformation efficiently. This reaction involves both a C-S bond activation and a C-C bond formation. The scalability, low catalyst and reagents loadings, and high functional group tolerance have enabled both late-stage derivatization and polymer recycling, demonstrating the reaction's utility across organic chemistry.
- Delcaillau, Tristan,Woenckhaus-Alvarez, Adrian,Morandi, Bill
-
supporting information
p. 7018 - 7022
(2021/09/13)
-
- Assembly of α-(Hetero)aryl Nitriles via Copper-Catalyzed Coupling Reactions with (Hetero)aryl Chlorides and Bromides
-
α-(Hetero)aryl nitriles are important structural motifs for pharmaceutical design. The known methods for direct synthesis of these compounds via coupling with (hetero)aryl halides suffer from narrow reaction scope. Herein, we report that the combination of copper salts and oxalic diamides enables the coupling of a variety of (hetero)aryl halides (Cl, Br) and ethyl cyanoacetate under mild conditions, affording α-(hetero)arylacetonitriles via one-pot decarboxylation. Additionally, the CuBr/oxalic diamide catalyzed coupling of (hetero)aryl bromides with α-alkyl-substituted ethyl cyanoacetates proceeds smoothly at 60 °C, leading to the formation of α-alkyl (hetero)arylacetonitriles after decarboxylation. The method features a general substrate scope and is compatible with various functionalities and heteroaryls.
- Chen, Ying,Xu, Lanting,Jiang, Yongwen,Ma, Dawei
-
supporting information
p. 7082 - 7086
(2021/02/26)
-
- Preparation method of 4-methylthio phenylacetic acid
-
The invention provides a preparation method of 4-methylthio phenylacetic acid. According to the preparation method, p-halogenated phenylacetic acid and phenylacetic acid derivatives thereof are taken as the primary raw materials. The preparation method is characterized in that p-halogenated phenylacetic acid and phenylacetic acid derivatives thereof and sodium methyl mercaptide carry out catalytic reactions in the presence of cuprous ions and DMF, and 4-methylthio phenylacetic acid is obtained after the post treatment. The Willgerodt-kindler reactions will generate hydrogen sulfide, which is pollutant to the environment, the provided method does not have Willgerodt-kindler reactions, and thus the environmental pollution is avoided. Moreover, the operation is simple, and the method is environment-friendly and is suitable for large-scale industrial production.
- -
-
Paragraph 0011
(2016/11/14)
-
- Synthesis of α-Aryl nitriles through palladium-catalyzed decarboxylative coupling of cyanoacetate salts with aryl halides and triflates
-
Worth its salt: The palladium-catalyzed decarboxylative coupling of the cyanoacetate salt as well as its mono- and disubstituted derivatives with aryl chlorides, bromides, and triflates is described (see scheme). This reaction is potentially useful for the preparation of a diverse array of α-aryl nitriles and has good functional group tolerance. S-Phos=2-(2,6- dimethoxybiphenyl)dicyclohexylphosphine), Xant-Phos=4,5-bis(diphenylphosphino)- 9,9-dimethylxanthene. Copyright
- Shang, Rui,Ji, Dong-Sheng,Chu, Ling,Fu, Yao,Liu, Lei
-
supporting information; experimental part
p. 4470 - 4474
(2011/06/24)
-
- Synthesis and selective cyclooxygenase-2 (COX-2) inhibitory activity of a series of novel bicyclic pyrazoles
-
Novel series of pyrazolo[5,1-b]1,3-oxazolidines, pyrazolo[5,1-b]1,3- oxazines and imidazolidino[1,2-d]pyrazoles were synthesized. These compounds were evaluated in vitro for their ability to inhibit cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) in human whole blood (HWB). Several of the compounds were found to be novel and selective COX-2 inhibitors, the most potent and selective being 1-(5-cyclohexyl (2H,3H-pyrazolo[5,1-b]-1,3- oxazolidin-6-yl)-4-(methylsulfonyl)benzene, 7a (IC5o for COX-1>100 μM; for COX-2=1.3 μM).
- Ranatunge, Ramani R.,Garvey, David S.,Janero, David R.,Letts, L. Gordon,Martino, Allison M.,Murty, Madhavi G.,Richardson, Stewart K.,Young, Delano V.,Zemetseva, Irina S.
-
p. 1357 - 1366
(2007/10/03)
-
- Sulfonamides and uses
-
Sulfonamides of formula I, in which the symbols R1 -R6, X, Y and n have the significance given in the description and which are in part novel compounds, and salts thereof, which can be used as active ingredients for the manufacture of medicaments for the treatment of circulatory disorders, especially hypertension, ischemia, vasospasms and angina pectoris, are described.
- -
-
-
- Displacement of Halogen of 2-Halogeno-Substituted Benzonitriles with Carbanions. Preparation of (2-Cyanoaryl)arylacetonitriles
-
(2-Cyanoaryl)arylacetonitriles are obtained by displacement of halogen of 2-halobenzonitriles with phenylacetonitrile anions.The method also applies to a number of heteroaromatics with ortho-situated halogen and cyano groups and to heteroarylacetonitrile anions.The anions were generated by using potassium tert-butoxide or potassium carbonate.Calculated electron densities of the electrophilic centers reflect the reactivity in the displacement reaction.The calculations indicate that the potassium ion complexes with the cyano group of the 2-halobenzonitriles in nonpolar solvents, thus promoting competitive addition of the anion to the cyano group.Carbanions derived from acids with pKa ca. 19-23 similarly displaced the halogen of 2-halobenzonitriles.
- Bech Sommer, Michael,Begtrup, Mikael,Boegesoe, Klaus Peter
-
p. 4817 - 4821
(2007/10/02)
-
- 2-aryl-ethyl ether derivatives and insecticidal and acaricidal agents containing said derivatives
-
The present invention relates to 2-arylethyl ether or thioether derivatives represented by the following general formula [I]: STR1 wherein Ar stands for an aryl group, R1 stands for straight or branched chain alkyl group of 1 to 6 carbons, R2 stands for a hydrogen atom, or a methyl or ethyl group, R3 stands for a halogen atom, or a methyl or methoxyl group, R4 stands for a hydrogen or halogen atom, or a lower alkyl or lower alkoxy group, and n is an integer of 1 or 2 with the proviso that when n is 2, the groups R4 may be the same or different, and Y stands for an oxygen or sulfur atom, and also to processes for the preparation of these ethers or thioethers and a use of these ethers or thioethers. These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicity of these compounds are very low.
- -
-
-
- 2-Arylpropyl ether or thioether derivatives and insecticidal and acaricidal agents containing said derivatives
-
The present invention relates to 2-arylpropyl ether or thioether derivatives represented by the following general formula [I]: STR1 wherein Ar stands for an aryl group, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula [II]: STR2 or the following general formula [III]: STR3 wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R1 may be the same or different, and also to processes for the preparation or these ethers of thioethers and a use of these ethers or thioethers. These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicity of these compounds are very low.
- -
-
-
- 1-Substituted aralkyl imidazoles
-
This disclosure describes novel aralkyl imidazoles, their acid addition salts, their metal complex salts and processes for their preparation. These compounds possess biological activity and in particular are useful as systemic protectant/eradicant fungicidal agents for controlling plant diseases caused by fungi and as plant growth regulators. The metal complex salts of these compounds are particularly useful in their ability to reduce undesirable plant growth regulatory activity and phytotoxicity while retaining their ability for controlling plant diseases caused by fungi.
- -
-
-