7187-01-1Relevant academic research and scientific papers
Preparation method of nitrile compound
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Paragraph 0072-0074, (2022/01/08)
The present invention belongs to the field of organic synthesis technology, specifically relates to a method for preparing a nitrile compound, aldehyde oxime derivatives as raw materials, adding DPPA and DBU, reacting in an organic solvent, one step to pr
Nickel-Catalyzed Transformation of Alkene-Tethered Oxime Ethers to Nitriles by a Traceless Directing Group Strategy
Takahashi, Yoshiyuki,Tsuji, Hiroaki,Kawatsura, Motoi
, p. 2654 - 2665 (2020/02/04)
Nickel-catalyzed transformation of alkene-tethered oxime ethers to nitriles using a traceless directing group strategy has been developed. A series of alkene-tethered oxime ethers derived from benzaldehyde and cinnamyl aldehyde derivatives were converted into the corresponding benzonitriles and cinnamonitriles in 46-98% yields using the nickel catalyst system. Control experiments showed that the alkene group tethered to an oxygen atom on the oximes via one methylene unit plays a key role as a traceless directing group during the catalysis.
Development and Utilization of a Palladium-Catalyzed Dehydration of Primary Amides to Form Nitriles
Al-Huniti, Mohammed H.,Rivera-Chávez, José,Colón, Katsuya L.,Stanley, Jarrod L.,Burdette, Joanna E.,Pearce, Cedric J.,Oberlies, Nicholas H.,Croatt, Mitchell P.
supporting information, p. 6046 - 6050 (2018/09/27)
A palladium(II) catalyst, in the presence of Selectfluor, enables the efficient and chemoselective transformation of primary amides into nitriles. The amides can be attached to aromatic rings, heteroaromatic rings, or aliphatic side chains, and the reactions tolerate steric bulk and electronic modification. Dehydration of a peptaibol containing three glutamine groups afforded structure-activity relationships for each glutamine residue. Thus, this dehydration can act similarly to an alanine scan for glutamines via synthetic mutation.
One-Pot Synthesis of α,β-Unsaturated Esters, Ketones, and Nitriles from Alcohols and Phosphonium Salts
Ding, Weijie,Hu, Juan,Jin, Huile,Yu, Xiaochun,Wang, Shun
, p. 107 - 118 (2017/09/28)
A general method for the synthesis of α,β-unsaturated esters, ketones, and nitriles is successfully achieved by a one-pot copper-catalyzed oxidation with O 2 in air as oxidant. The solvent mixture of acetonitrile and formamide (1:1) is optimized to ensure the oxidation of alcohols, deprotonation of phosphonium salt, and Wittig reaction occur efficiently in one pot. A broad range of substrates has been explored for this process, including three electron-withdrawing group (CO 2 Et, COPh, CN) functionalized phosphonium salts. They reacted not only with benzylic and heteroaromatic alcohols, but also with aliphatic alcohols, forming the corresponding α,β-unsaturated esters, ketones, and nitriles in moderate to excellent yields.
Selective and facile synthesis of α,β-unsaturated nitriles and amides with N-hydroxyphthalimide as the nitrogen source
Yan, Yiyan,Xu, Xiaohe,Jie, Xiaokang,Cheng, Jingya,Bai, Renren,Shuai, Qi,Xie, Yuanyuan
supporting information, p. 2793 - 2796 (2018/06/25)
The direct conversion of α,β-unsaturated aldehydes to corresponding nitriles promoted by Pd(OAc)2 and phthalic acid which was hydrolyzed from N-hydroxyphthalimide (NHPI) has been disclosed. Additionally, it was found that when water was used as the solvent, α,β-unsaturated amides was obtained as the main products in good to excellent yields. It was first reported that NHPI was utilized as the nitrogen source to synthesize α,β-unsaturated nitriles and amides from aldehydes. Control experiment demonstrated that aldehydes undergo a process of oximation and dehydration to form nitriles and amides.
Stable and reusable nanoscale Fe2O3-catalyzed aerobic oxidation process for the selective synthesis of nitriles and primary amides
Murugesan, Kathiravan,Senthamarai, Thirusangumurugan,Sohail, Manzar,Sharif, Muhammad,Kalevaru, Narayana V.,Jagadeesh, Rajenahally V.
supporting information, p. 266 - 273 (2018/01/12)
The sustainable introduction of nitrogen moieties in the form of nitrile or amide groups in functionalized molecules is of fundamental interest because nitrogen-containing motifs are found in a large number of life science molecules, natural products and materials. Hence, the synthesis and functionalization of nitriles and amides from easily available starting materials using cost-effective catalysts and green reagents is highly desired. In this regard, herein we report the nanoscale iron oxide-catalyzed environmentally benign synthesis of nitriles and primary amides from aldehydes and aqueous ammonia in the presence of 1 bar O2 or air. Under mild reaction conditions, this iron-catalyzed aerobic oxidation process proceeds to synthesise functionalized and structurally diverse aromatic, aliphatic and heterocyclic nitriles. Additionally, applying this iron-based protocol, primary amides have also been prepared in a water medium.
Preparation method of trans-alpha, beta-unsaturated nitriles compound
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Paragraph 0066-0068, (2017/05/18)
The invention relates to a preparation method of a trans-alpha, beta-unsaturated nitriles compound. The method comprises the following steps: uniformly mixing a benzyl alcohol compound, acetonitrile, a promoter and alkali, and carrying out reflux reaction completely to obtain reaction liquid; carrying out conventional extraction, drying, concentration and column chromatographic separation on the reaction liquid in sequence to obtain the trans-alpha, beta-unsaturated nitriles compound. The preparation method belongs to double-component one-boiler reaction, so that conditions are relatively mild, and raw materials are easy to prepare and readily available; the operation is simple, the yield is relatively high, and greenness, environment friendliness and economy can be realized; large-scale production can be realized; the preparation method has an extremely good application potential on the aspect of fine chemicals, and has a relatively good industrial application prospect.
Associative Covalent Relay: An Oxadiazolone Strategy for Rhodium(III)-Catalyzed Synthesis of Primary Pyridinylamines
Yu, Xiaolong,Chen, Kehao,Wang, Qi,Guo, Shan,Zha, Shanke,Zhu, Jin
supporting information, p. 5222 - 5226 (2017/04/27)
A relay formalism is proposed herein for categorizing the interplay among reactants, target product, and catalytic center in transition-metal catalysis, an important factor that can dictate overall catalysis viability and efficiency. In this formalism, transition-metal catalysis can proceed by dissociative relay, associative covalent relay, and associative dative relay modes. An intriguing associative covalent relay process operates in rhodium(III)-catalyzed oxadiazolone-directed alkenyl C?H coupling with alkynes and allows efficient access to primary pyridinylamines. Although the primary pyridinylamine synthesis mechanism is posteriori rationalized, the relay formalism formulated herein can provide an important mechanistic conceptual framework for future catalyst design and reaction development.
Rhodium(III)-catalyzed oxadiazole-directed alkenyl C-H activation for synthetic access to 2-acylamino and 2-amino pyridines
Yang, Fan,Yu, Jiaojiao,Liu, Yun,Zhu, Jin
supporting information, p. 9978 - 9987 (2018/05/31)
We report herein a Rh(III)-catalyzed alkenyl C-H activation protocol for the coupling of oxadiazoles with alkynes and synthesis of 2- acylamino and 2-amino pyridines, an important heterocyclic scaffold for various naturals products and synthetic pharmaceuticals bearing a readily reacting functional group. The selective protection/deprotection of amino groups through simple solvent switching, good functional group compatibility, superior product yield, and high regioselectivity are some of the notable synthetic features witnessed in this reaction protocol.
