903556-80-9Relevant academic research and scientific papers
Late-stage Pd-catalyzed Cyanations of Aryl/Heteroaryl Halides in Aqueous Micellar Media
Thakore, Ruchita R.,Takale, Balaram S.,Singhania, Vani,Gallou, Fabrice,Lipshutz, Bruce H.
, p. 212 - 216 (2020/12/01)
New technology is described that enables late stage ppm Pd-catalyzed cyanations of highly complex molecules, as well as a wide variety of aryl and heteroaryl halides possessing sensitive functional groups. These reactions are efficient in water containing nanomicelles, formed from a commercially available and inexpensive surfactant. The implications for advancing drug synthesis and discovery are apparent.
Nickel-catalyzed cyanation of aryl halides and triflates using acetonitrile: Via C-CN bond cleavage assisted by 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine
Ueda, Yohei,Tsujimoto, Nagataka,Yurino, Taiga,Tsurugi, Hayato,Mashima, Kazushi
, p. 994 - 999 (2019/02/03)
We developed a non-toxic cyanation reaction of various aryl halides and triflates in acetonitrile using a catalyst system of [Ni(MeCN)6](BF4)2, 1,10-phenanthroline, and 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine (Si-Me4-DHP). Si-Me4-DHP was found to function as a reductant for generating nickel(0) species and a silylation reagent to achieve the catalytic cyanation via C-CN bond cleavage.
Preparation method of aromatic nitrile compound or heteroaromatic nitrile compound
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Paragraph 0043; 0045; 0219-0221, (2018/11/03)
The invention discloses a preparation method of an aromatic nitrile compound or a heteroaromatic nitrile compound. The preparation method comprises: under the protection of an inert gas, in a solvent,under the actions of a nickel catalyst, a ligand, metal zinc and an additive, carrying out a reaction on a cyanation reagent and halogenated aromatic hydrocarbon or halogenated heteroaromatic hydrocarbon. According to the present invention, by using the inexpensive and easily-available nickel catalyst and the ligand, the halogenated aromatic hydrocarbon or halogenated heteroaromatic hydrocarbon,especially the chlorinated aromatic hydrocarbon or chlorinated heteroaromatic hydrocarbon with characteristics of low price, easy obtaining and low reaction activity can mildly and efficiently react with the cyanation reagent with low toxicity to prepare the aromatic nitrile compound or heteroaromatic nitrile compound; and the preparation method has advantages of simple operation, mildness, high efficiency and the like, and further has characteristics of good functional group compatibility, good universality of substrate and the like.
A benzoxazole derivative synthesis method
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Paragraph 0056; 0058; 0059, (2017/08/25)
A synthetic method of benzoxazole derivative belongs to the technical field of organic chemistry synthesis. Raw material of a variety of o-hydroxyphenyl ketimines, an oxidant of iodobenzene diacetate and an additive of alkali are subjected to a simple process comprising one-step oxidation rearrangement, concentration and purification in a solvent at room temperature to obtain a product. This method has the characteristics of certain universality, mild reaction conditions, low production equipment requirement, simple technology, easily obtained raw materials, short reaction time and higher efficiency. Benzoxazole derivative products with high yield and good quality can be prepared by adopting the method of the invention; the method can be widely used in industrial production of benzoxazole derivatives; the products prepared by the method of the invention can be widely used as fluorescent whitening agents, dyeing agents, preservatives, rubber vulcanization accelerators and organic electroluminescent materials, as well as antistatic agent for the plastic films; therefore, the invention has good market application prospects.
General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN)2: Key Roles of DMAP
Zhang, Xingjie,Xia, Aiyou,Chen, Haoyi,Liu, Yuanhong
supporting information, p. 2118 - 2121 (2017/04/27)
A new and general nickel-catalyzed cyanation of hetero(aryl) chlorides using less toxic Zn(CN)2 as the cyanide source has been developed. The reaction relies on the use of inexpensive NiCl2·6H2O/dppf/Zn as the catalytic system and DMAP as the additive, allowing the cyanation to occur under mild reaction conditions (50-80 °C) with wide functional group tolerance. DMAP was found to be crucial for successful transformation, and the reaction likely proceeds via a Ni(0)/Ni(II) catalysis based on mechanistic studies. The method was also successfully extended to aryl bromides and aryl iodides.
Hypervalent iodine-mediated synthesis of benzoxazoles and benzimidazoles via an oxidative rearrangement
Zhang, Xiaohui,Huang, Ruofeng,Marrot, Jér?me,Coeffard, Vincent,Xiong, Yan
, p. 700 - 708 (2015/02/02)
A Beckmann-type rearrangement of o-hydroxy and o-aminoaryl N-H ketimines has been developed to prepare benzoxazoles and N-Ts benzimidazoles, respectively. The ketimine derivatives were easily prepared by condensation of ammonia with the corresponding ketones and (diacetoxyiodo)benzene was found to act as an efficient oxidant to trigger the [1,2]-aryl migration towards the formation of the desired heterocycles. Depending on the substitution pattern, the results revealed another mechanistic pathway through which benzisoxazoles or 1H-indazoles could be formed. The Beckmann-type rearrangement strategy was applied to the synthesis of benzimidazole-containing biorelevant targets such as chlormidazole and clemizole.
Mild palladium-catalyzed cyanation of (hetero)aryl halides and triflates in aqueous media
Cohen, Daniel T.,Buchwald, Stephen L.
supporting information, p. 202 - 205 (2015/01/30)
A mild, efficient, and low-temperature palladium-catalyzed cyanation of (hetero)aryl halides and triflates is reported. Previous palladium-catalyzed cyanations of (hetero)aryl halides have required higher temperatures to achieve good catalytic activity. This current reaction allows the cyanation of a general scope of (hetero)aryl halides and triflates at 2-5 mol % catalyst loadings with temperatures ranging from rt to 40 °C. This mild method was applied to the synthesis of lersivirine, a reverse transcriptase inhibitor.
Substituted bis-amide metalloprotease inhibitors
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Page/Page column 32-33, (2010/11/27)
This invention relates to substituted bis-amide pyrimidine compounds of Formula (I), which are useful for the treatment of metalloprotease mediated diseases, in particular MMP-13 related diseases.
Multicyclic bis-amide MMP inhibitors
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Page/Page column 98, (2008/06/13)
The present invention relates generally to bis-amide group containing pharmaceutical agents, and in particular, to multicyclic bis-amide MMP-13 inhibitor compounds. More particularly, the present invention provides a new class of MMP-13 inhibiting compounds, containing a pyrimidinyl bis-amide group in combination with a heterocyclic moiety, that exhibit an increased potency and solubility in relation to currently known bis-amide group containing MMP-13 inhibitors.
