23826-56-4Relevant academic research and scientific papers
Gold-Catalyzed Oxidation of Internal Alkynes into Benzils and its Application for One-Pot Synthesis of Five-, Six-, and Seven-Membered Azaheterocycles
Dubovtsev, Alexey Yu.,Dar'in, Dmitry V.,Krasavin, Mikhail,Kukushkin, Vadim Yu.
, p. 1856 - 1864 (2019/02/19)
Internal alkynes have been shown to undergo oxidation to substituted benzils (1,2-diarylethane-1,2-diones) by α-picoline N-oxide in the presence of Ph3PAuNТf2 (5 mol-%). In addition to the unsubstituted benzil, the method allows preparing, under markedly mild conditions (50 °C in chlorobenzene), various non-symmetrical products, including heteroaromatic versions thereof which are much more difficult to obtain otherwise. This gold(I)-catalyzed transformation was integrated into one-pot reaction sequence delivering a range of 5- to 7-membered ring systems (imidazoles, quinoxalines, 1,2,4-triazines, pyrazines, and 1,4-diazepines), thus linking these important heterocyclic motifs to the internal alkyne reagent space.
Electrochemical synthesis of 1,2-diketones from alkynes under transition-metal-catalyst-free conditions
Zhou, Jie,Tao, Xiang-Zhang,Dai, Jian-Jun,Li, Chen-Guang,Xu, Jun,Xu, Hong-Mei,Xu, Hua-Jian
supporting information, p. 9208 - 9211 (2019/08/07)
We report an electrochemical protocol for the direct oxidation of internal alkynes in air to provide 1,2-diketones. A variety of functional groups and heterocycle-containing substrates can be tolerated well under mild conditions.
B2pin2-mediated copper-catalyzed oxidation of alkynes into 1,2-diketones using molecular oxygen
Zhai, Yadong,Su, Zhenni,Jiang, Hao,Rong, Jing,Qiu, Xianfan,Tao, Chuanzhou
supporting information, p. 843 - 846 (2019/02/19)
An intriguing aerobic oxidation of alkynes through copper catalysis is described, in which bis(pinacolato)diboron (B2pin2) played a dominant intermediary role in the formation 1,2-diketones. This novel protocol, which can be performed at room temperature, is versatile for various substituted alkynes, including diarylalkynes and arylalkylalkynes. The mechanism of this reaction was preliminarily investigated by control experiments.
Metal-Free Iodine-Catalyzed Oxidation of Ynamides and Diaryl Acetylenes into 1,2-Diketo Compounds
Kim, Seung Woo,Um, Tae-Woong,Shin, Seunghoon
supporting information, p. 4703 - 4711 (2018/04/26)
Metal-free oxidation of ynamides is described, employing pyridine-N-oxides as oxidants under molecular iodine catalysis. In stark contrast to Br?nsted acid catalysis, iodophilic activation of ynamides diverts the reaction manifold into a dioxygenation pathway. This oxidation is very rapid at room temperature with only 2.5 mol % I2. Furthermore, this protocol could be extended to nonactivated alkynes, such as diarylacetylenes, to deliver various benzil derivatives.
Two-Step One-Pot Synthesis of Unsymmetrical (Hetero)Aryl 1,2-Diketones by Addition-Oxygenation of Potassium Aryltrifluoroborates to (Hetero)Arylacetonitriles
Kumar, Yogesh,Jaiswal, Yogesh,Kumar, Amit
, p. 494 - 505 (2018/02/09)
An efficient one-pot two-step procedure for the synthesis of unsymmetrical (hetero)aryl 1,2-diketones has been developed. The reaction proceeds through a palladium-catalyzed nucleophilic addition of potassium aryltrifluoroborates to aliphatic nitriles followed by a copper-catalyzed aerobic benzylic C–H oxygenation using molecular oxygen as a green oxidant. This represents the first example of the direct synthesis of unsymmetrical diaryl 1,2-diketones from arylacetonitriles. This method utilizes inexpensive, stable, nontoxic, and readily available starting materials, is highly effective in the presence of both electron-rich and electron-poor nitriles and aryltrifluoroborates, and tolerates a wide variety of functional groups. The synthetic utility of this transformation was shown by increasing the scale of the reaction and by carrying out the one-pot protocol for the preparation of quinoxaline and benzimidazole derivatives. A plausible reaction mechanism has also been proposed.
Copper-catalyzed synthesis of 1,2-diketones via oxidation of alkynes
Xu, Ning,Gu, Da-Wei,Dong, Yan-Sheng,Yi, Feng-Ping,Cai, Liangzhen,Wu, Xin-Yan,Guo, Xun-Xiang
supporting information, p. 1517 - 1519 (2015/03/14)
The direct oxidation of internal alkynes proceeds efficiently in the presence of CuI as a catalyst to afford the corresponding 1,2-diketones in good yields. This strategy offers a simple and efficient route for the synthesis of 1,2-diketones from an inexpensive copper catalyst and easily available internal alkynes. The advantage of present protocol is further demonstrated by the synthesis of quinoxaline derivatives from alkynes and 1,2-diaminobenzene via one-pot procedure.
Efficient synthetic route to bisaryl ketones via copper-catalyzed C-C triple bonds cleavage
Li, Xiangguang,Huang, Wenzhong,Liang, Deqiang,Yuan, Lin,Ma, Yinhai,Gu, Lijun
, p. 1045 - 1049 (2015/01/30)
An efficient copper-catalyzed aerobic synthesis of bisaryl ketones from 1,2-diarylalkynes via C-C triple bonds cleavage has been demonstrated. The aniline compounds were found to be crucial in our conditions and a plausible mechanism was put forward. This reaction constitutes a new transformation from 1,2-diarylalkynes into bisaryl ketones with a practical, neutral, and mild synthetic approach.
Pd/Cu-catalyzed oxidation of alkynes into 1,2-diketones using DMSO as the oxidant
Gao, Ang,Yang, Fan,Li, Ji,Wu, Yangjie
experimental part, p. 4950 - 4954 (2012/07/30)
A facile and practical method for the palladium/copper-catalyzed transformation of internal alkynes into 1,2-diketones has been described, affording the desired products in moderate to excellent yields. The mechanistic studies were also preliminarily pursued using diphenyl sulfoxide as the oxidant, and the diphenyl sulfide was isolated as the reduced product.
Facile aerobic photo-oxidative synthesis of α-diketones from alkynes
Nobuta, Tomoya,Tada, Norihiro,Hattori, Kasumi,Hirashima, Shin-Ichi,Miura, Tsuyoshi,Itoh, Akichika
experimental part, p. 875 - 877 (2011/03/20)
We report a useful method for facile aerobic photo-oxidative synthesis of α-diketones from alkynes with MgBr2·OEt2. This procedure provides a practical synthetic method of α-diketones using easily handled bromine sources, harmless visible light, and molecular oxygen as terminal oxidant.
Amino-5-(6-membered)heteroarylimidazolone compounds and the use thereof for beta-secretase modulation
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Page/Page column 15, (2008/06/13)
The present invention provides a 2-amino-5-heteroaryl-5-phenylimidazolone compound of formula I The present invention also provides methods for the use thereof to inhibit β-secretase (BACE) and treat β-amyloid deposits and neurofibrillary tangles
