3063-79-4Relevant academic research and scientific papers
Synthetic method of N - aryl substituted lactam compound
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Paragraph 0047-0049, (2021/08/25)
The invention discloses a method. NSynthesis method of - aryl substituted lactam compound, and synthesis method thereof is promoted by tertiary butyl hydroperoxide and-tert-butyl hydroperoxideNMulti-step series reaction synthesis - aryl substituted saturated cyclic amine compoundN- Aryl substituted lactam compounds are simple and convenient to operate. The method has the advantages of no transition metal catalysis, wide substrate application range and the like, and is suitable for industrial production.
Ruthenium-catalyzed synthesis of: N -substituted lactams by acceptorless dehydrogenative coupling of diols with primary amines
Zheng, Yanling,Nie, Xufeng,Long, Yang,Ji, Li,Fu, Haiyan,Zheng, Xueli,Chen, Hua,Li, Ruixiang
supporting information, p. 12384 - 12387 (2019/10/19)
Herein, we report the first example of synthesis of N-substituted lactams via an acceptorless dehydrogenative coupling of diols with primary amines in one step, which was enabled by combining Ru3(CO)12 with a hybrid N-heterocyclic carbene-phosphine-phosphine ligand as the catalyst.
PIFA-Promoted, Solvent-Controlled Selective Functionalization of C(sp2)-H or C(sp3)-H: Nitration via C-N Bond Cleavage of CH3NO2, Cyanation, or Oxygenation in Water
Mudithanapelli, Chandrashekar,Dhorma, Lama Prema,Kim, Mi-Hyun
, (2019/05/07)
A novel nitration (via C(sp3)-N breaking/C(sp2)-N formation with CH3NO2) mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA) is described. The NO2 transfer from CH3NO2 to the aromatic group of the substrate is possible with careful selection of the solvent, NaX, and oxidant. In addition, the solvent-controlled C(sp2)-H functionalization can shift to an α-C(sp3)-H functionalization (cyanation or oxygenation) of the α-C(sp3)-H of cyclic amines.
Amidation of Aryl Chlorides Using a Microwave-Assisted, Copper-Catalyzed Concurrent Tandem Catalytic Methodology
Chang, Raymond K.,Clairmont, Brice P.,Lin, Shirley,MacArthur, Amy H. Roy
supporting information, p. 4448 - 4454 (2019/11/13)
A concurrent tandem catalytic (CTC) methodology has been developed for the amidation of aryl chlorides where the aryl chloride is first converted to an aryl iodide via halogen exchange and the aryl iodide is subsequently transformed into the aryl amide. A variety of aryl chlorides were converted to aryl amides in up to 85% isolated yield using 20 mol % CuI, 60 mol % N,N′-cyclohexane-1,2-diamine, 2.2 equiv of K2CO3, and 1.05-1.5 equiv of amide in acetonitrile at 200 °C after 0.75-1 h. The same copper/ligand system served as multifunctional catalyst for both steps of the concurrent catalytic process with iodide present in substoichiometric amounts. Mechanistic studies were consistent with CTC amidation occurring via a nonradical mechanism. Kinetic modeling was conducted to investigate the effect of competitive direct amidation of an aryl chloride or aryl bromide on the formation of product over time during a CTC amidation reaction.
Selective synthesis of pyrrolidin-2-ones and 3-iodopyrroles: Via the ring contraction and deformylative functionalization of piperidine derivatives
Wang, Fang,Zhang, Xinying,He, Yan,Fan, Xuesen
, p. 156 - 164 (2019/01/08)
In this paper, a selective synthesis of pyrrolidin-2-ones and 3-iodopyrroles via the cascade reactions of N-substituted piperidines is presented. Mechanistically, the formation of pyrrolidin-2-ones involves a domino process including the in situ formation of pyrrolidine-2-carbaldehyde followed by carboxylic acid formation, decarboxylation and ipso-oxidation. On the other hand, 3-iodopyrroles are believed to be formed via the initial generation of pyrrolidine-2-carbaldehyde followed by carboxylic acid formation, decarboxylation, dehydrogenation, iodination and aromatization. Interestingly, either pyrrolidin-2-ones or 3-iodopyrroles could be obtained selectively from the same substrates, and the selectivity was easily tuned by using a specific oxidant and additive.
Pyrrolidone compound synthesis method
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Paragraph 0054-0056, (2019/03/08)
The invention discloses a pyrrolidone compound synthesis method, and belongs to the technical field of organic synthesis. Saturated cyclic tertiary amine 1 is added into solvents, and heating reactionis performed in the presence of oxidizing agent, cupric salt, potassium hydrogen persulfate compound salt (Oxone) and oxygen mixture, additives, elementary iodine or iodated metal salt and the like to obtain pyrrolidone 2. According to the method, a pyrrolidone compound is synthesized by cascade reaction of oxidization retraction, decarbonylation and in-situ oxidization of saturated cyclic tertiary amine compounds, the method has the advantages of simplicity and convenience in operation, mild conditions, wide substrate application range and the like, and an economical, practical, green and environment-friendly novel method is provided for synthesis of the pyrrolidone compound.
Ligand-Enabled Gold-Catalyzed C(sp2)-N Cross-Coupling Reactions of Aryl Iodides with Amines
Akram, Manjur O.,Das, Avishek,Chakrabarty, Indradweep,Patil, Nitin T.
supporting information, p. 8101 - 8105 (2019/10/11)
The first example of ancillary (P,N)-ligand-enabled gold-catalyzed C-N cross-coupling reactions of aryl iodides with amines is reported. The high generality of the reaction in de novo synthesis, late-stage modifications, and cascade processes to access functionalized indolinones and carbazoles underscores the synthetic potential of the presented strategy. Monitoring the reaction with ESI-HRMS and NMR provided strong evidence for the in situ formation of putative high valent Au(III) intermediates.
Aluminium Chloride-Mediated Synthesis of 1-Chloro-2,2,2-Trifluoroethylidene-Substituted Pyrrolidones
Wang, Zeng,Yuan, Zihang,Han, Xiaoyan,Weng, Zhiqiang
supporting information, p. 2178 - 2182 (2018/04/25)
An aluminium chloride-mediated cascade reaction between pyrrolidones and trifluoroacetic anhydride is reported. Functionally diverse 1-chloro-2,2,2-trifluoroethylidene-substituted pyrrolidones were obtained in moderate to high yields through electrophilic trifluoroacetylation, nucleophilic chlorination, and elimination. This procedure has a wide scope, good functional-group tolerance and the reaction conditions are amenable to scale up. Additionally the obtained 1-chloro-2,2,2-trifluoroethylidene products can be applied to further functionalization as trifluoromethyl-containing building blocks. Some of the title compounds showed fungicidal activity against cucumber downy mildew (CDM). (Figure presented.).
Copper-Catalyzed Coupling Reaction of (Hetero)Aryl Chlorides and Amides
De, Subhadip,Yin, Junli,Ma, Dawei
supporting information, p. 4864 - 4867 (2017/09/23)
Cu2O/N,N′-bis(thiophen-2-ylmethyl)oxalamide is established to be an effective catalyst system for Goldberg amidation with inferior reactive (hetero)aryl chlorides, which have not been efficiently documented by Cu-catalysis to date. The reaction is well liberalized toward a variety of functionalized (hetero)aryl chlorides and a wide range of aromatic and aliphatic primary amides in good to excellent yields. Furthermore, the arylation of lactams and oxazolidinones is achieved. The present catalytic system also accomplished an intramolecular cross-coupling product.
Efficient Synthesis of N-Substituted 2,4-Azepandione Ring System as an Active Intermediate for Heterocyclic Syntheses
Waly, Mohamed A.,Yossif, Shiam A.,Ibrahim, Ismail T.,Sofan, Mamdouh A.
, p. 1318 - 1326 (2017/03/27)
An improved efficient synthesis for 2,4-azepandiones (3, 8, and 14) could be achieved by a careful control of the reaction conditions to cyclize ethyl 4-(N-acetylarylamino) butanoate (1, 7, and 13), respectively. The ethyl 4-arylamino butanoate (9 or 12) was prepared by stirring the ethyl 4-bromobutanoate and substituted anilines at room temperature. Then, they were acetylated with acetyl chloride and triethylamine under the conditions that avoid the formation of 2-pyrrolidinone derivatives 10. Due to the rapid decomposition of the acetylated product (7 or 13) to its starting material (9 or 12), the reaction mixture is directly transferred without workup to the next cyclization step. The azepandione synthesis is favored by using a weak base at low temperature, where it is in a competition with the other modes of ring closure. The structures of the new compounds were supported by correct analytical and spectral data.
