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Synthetic method of N - aryl substituted lactam compound
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Paragraph 0065-0067, (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.
Method for synthesizing cyclic amide from carbon dioxide
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Paragraph 0017, (2019/12/29)
The invention discloses a method for synthesizing cyclic amide from carbon dioxide. An aromatic amino compound, 1 atm carbon dioxide and a halogenated compound undergo a one-step reaction under the synergistic action of N-doped TiO2 and an inorganic salt catalyst to generate the cyclic amide. Studies find that visible light has an obvious promoting effect on the conversion process. The chemical selectivity of the cyclic amide compound can be regulated by regulating conditions such as reaction temperature, time and illumination. The catalyst can be recycled for five times after being separatedand dried, and the activity and the chemical selectivity can be well maintained. The synthesis method has the advantages of simple synthetic route, novelty, simple process, high yield and high purityof the product, cheap and easily available catalyst, no influences on the environment, and suitableness for industrial production.
A general catalytic methylation of amines using carbon dioxide
Li, Yuehui,Fang, Xianjie,Junge, Kathrin,Beller, Matthias
supporting information, p. 9568 - 9571 (2013/09/23)
Putting CO2 to work: Carbon dioxide is shown to be a general and selective methylating reagent for secondary and primary, aromatic and aliphatic amines under reductive conditions. A variety of tertiary amines are obtained from CO2 and commercially available silanes in high yields with good tolerance to nitrile, olefin, ether, ester, and hydroxy groups. Copyright
Complementation of biotransformations with chemical C-H oxidation: Copper-catalyzed oxidation of tertiary amines in complex pharmaceuticals
Genovino, Julien,Luetz, Stephan,Sames, Dalibor,Toure, B. Barry
supporting information, p. 12346 - 12352 (2013/09/23)
The isolation, quantitation, and characterization of drug metabolites in biological fluids remain challenging. Rapid access to oxidized drugs could facilitate metabolite identification and enable early pharmacology and toxicity studies. Herein, we compared biotransformations to classical and new chemical C-H oxidation methods using oxcarbazepine, naproxen, and an early compound hit (phthalazine 1). These studies illustrated the low preparative efficacy of biotransformations and the inability of chemical methods to oxidize complex pharmaceuticals. We also disclose an aerobic catalytic protocole (CuI/air) to oxidize tertiary amines and benzylic CH's in drugs. The reaction tolerates a broad range of functionalities and displays a high level of chemoselectivity, which is not generally explained by the strength of the C-H bonds but by the individual structural chemotype. This study represents a first step toward establishing a chemical toolkit (chemotransformations) that can selectively oxidize C-H bonds in complex pharmaceuticals and rapidly deliver drug metabolites.
Mild, convenient and versatile Cu-mediated synthesis of N-aryl-2-imidazolidinones
Stabile, Paolo,Lamonica, Alessandro,Ribecai, Arianna,Castoldi, Damiano,Guercio, Giuseppe,Curcuruto, Ornella
scheme or table, p. 3232 - 3235 (2010/08/07)
A mild, general, convenient and practical methodology for the selective copper-mediated mono N-arylation of unprotected 2-imidazolidinone was developed. Strong electron-donating groups and free hydroxy and amino groups on the aryl iodide substrates were well tolerated. The use of n-butanol as the solvent for the copper-catalysed mono-arylation of 2-imidazolidinone is unprecedented.
Synthesis of symmetrical and unsymmetrical N-aryl-substituted cyclic ureas through copper(I) iodide catalyzed Goldberg-Buchwald-Nandakumar C-N coupling reactions
Lee, Chung-Chieh,Wang, Po-Shih,Viswanath, M. Balaji,Leung, Man-Kit
, p. 1359 - 1366 (2008/12/21)
The catalytic conditions of copper(I) iodide/potassium carbonate/trans-N, N′-dimethylcyclohexane-1,2-diamine, either in toluene at reflux temperature, or by heating neat at 150°C effectively promoted the C-N coupling of aryl bromides with cyclic ureas. By
[3+2] Cross-coupling reactions of aziridines with isocyanates catalyzed by nickel(II) iodide
Munegumi, Takeshi,Azumaya, Isao,Kato, Takako,Masu, Hyuma,Saito, Shinichi
, p. 379 - 382 (2007/10/03)
Cycloaddition of aziridines with isocyanates proceeded smoothly in the presence of a nickel catalyst, and five iminooxazolidine derivatives were isolated in good yields. The best result was obtained when the reaction was carried out in the presence of NiI
Chemistry of free cyclic vicinal tricarbonyl compounds ('1,2,3-triones'). Part 2. Redox reactions of 1,2,3-triones with ene-1,2-diols ('reductones'), 2-alkoxy-en-1-ols, ene-1,2-diamines, and related species
Schank, Kurt,Bouillon, Guenter,Fuenfrocken, Michael,Lick, Carlo,Lieder, Robert
, p. 1295 - 1326 (2007/10/03)
Midstanding carbonyl groups of cyclic 1,2,3-triones 4 possess outstanding electrophilic (electron-pair accepting) as well as oxidizing (one-electron accepting) properties. Their reactions with selected electron-rich C=C bonds as efficient nucleophiles AN reactions) and as efficient reducing agents (SET (single electron transfer) reactions) are studied. In a few cases, short-lived charge-transfer colors be observed. Particularly, free didehydro-5,6-O-isopropyliden-L-ascorbic acid (4g), its O,C-adduct 8g to 5,6-O-isopropylidene-L-ascorbic acid (1g), and via an independent pathway - the ostensible C,C-dimer 10a of mono-dehydrodimedone reductone were prepared. Intermediate radical anions 4 can be considered to be ideal representatives of dicapto-dative radicals. Novel large-scale syntheses of 3,4-dihydroxyfuran-2(5H)-one (1e) and of its vicinal trione 4e are presented.
Extremely Reactive C=C Double Bonds, V. - 2--1,3-diphenylimidazolidine, a Tetraaminoethylene of a New Type
Schoenberg, Alexander,Singer, Erich,Stephan, Werner
, p. 1589 - 1592 (2007/10/02)
The synthesis of the title compound 3 by two different routes and some reactions are described.The mechanisms of formation are discussed.
THIONO COMPOUNDS. 5. PREPARATION AND OXIDATION OF SOME THIONO DERIVATIVES OF IMIDAZOLES
Karkhanis, Dattatraya W.,Field, Lamar
, p. 49 - 58 (2007/10/02)
1,3-Dimethyl-3H-imidazole-2-thione (3), prepared by a much improved procedure from 1,3-dimethylimidazolium iodide (6) with sulfur and organic base, was oxidized with H2O2 in MeOH; three molar proportions of H2O2 were consumed, 1,3-dimethylimidazolium picrate (14; synthesized independently) was isolated in 61percent yield, and 80percent of the expected sulfate ion was found.Oxidation of the analogous imidazolidine (4), prepared from 1,3-dimethyl-2-imidazolidone (16) with Lawesson's reagent (17), gave a counterpart picrate (73percent from 4) in a similar but slower reaction. 1,3-Diphenyl-2-imidazolidinethione (5) had to be oxidized in DMF-AcOH, with H2SO4 catalysis, and only 1,3-diphenyl-2-imidazolidone (19, 63percent) could be isolated.Understanding is added to the behavior in oxidations of thiono derivatives of imidazoles by these extensions of several earlier studies to different types within the class, i.e., of an N-unsubstituted one (1) to the N,N-dimethyl counterpart (4), of an N-methyl unsaturated one (2) to the N,N-dimethyl counterpart (3), and of an N,N-diphenyl unsaturated one (23) to the saturated counterpart (5).Similarities and differences are discussed relative to members of the class studied previously, along with information that improves understanding of the different courses of reactions various members of the class may follow when they are oxidized.
