- One-Pot Synthesis of Disubstituted Urea from Carbon Dioxide, Propylene Oxide, and Amines Catalyzed by Imidazolium-Tetraiodoindate
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In this article, synthesis of 1,3-disubstituted urea (DSU) from three component reagent systems comprising amine, carbon dioxide, and propylene oxide is described. DSU is synthesized in the presence of a variety of ionic liquids (ILs) with/without promoters. Among used ILs, 1-butyl-3-methylimidazolium tetraiodoindateIII (represented as [Bmim][InI4]) is found to give the highest DSU product. A serious experiment clearly indicates that the tetraiodoindate anion plays an important role for the selective production of the DSU. Based on the in situ infrared spectroscopic studies, a plausible reaction mechanism for producing dicyclohexylurea from cyclohexylamine is proposed. The synthesis and characterization of [Bmim][InI4] are given in details. Moreover, the effect of reaction variables such as time, temperature, pressure, and the molar ratio of substrate to catalyst is also studied.
- Son, Guang Meang,Truong, Cong Chien,Mishra, Dinesh Kumar,Mishra, Vivek,Kim, Yong Jin
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- Anti-Markovnikov Hydroamination of Unactivated Alkenes with Primary Alkyl Amines
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We report here a photocatalytic method for the intermolecular anti-Markovnikov hydroamination of unactivated olefins with primary alkyl amines to selectively furnish secondary amine products. These reactions proceed through aminium radical cation (ARC) intermediates and occur at room temperature under visible light irradiation in the presence of an iridium photocatalyst and an aryl thiol hydrogen atom donor. Despite the presence of excess olefin, high selectivities are observed for secondary over tertiary amine products, even though the secondary amines are established substrates for ARC-based olefin amination under similar conditions.
- Miller, David C.,Ganley, Jacob M.,Musacchio, Andrew J.,Sherwood, Trevor C.,Ewing, William R.,Knowles, Robert R.
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supporting information
p. 16590 - 16594
(2019/11/03)
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- Process for Preparing Disubstituted Urea and Carbamate Compounds from Amines, Carbon Dioxide, and Epoxides
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The present disclosure relates to a method for preparing a disubstituted urea and carbamate compounds simultaneously through a one-pot reaction of an amine, carbon dioxide and an alkylene oxide compound in the presence of an ionic liquid-based complex catalyst system containing indium. In accordance with the present disclosure, a disubstituted urea and carbamate compounds can be prepared simultaneously at high yield. In addition, the ionic liquid-based catalyst containing indium according to the present disclosure is economical because it can be reused several times.
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Paragraph 0061; 0062; 0063
(2015/05/26)
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- Syntheses of five- and seven-membered ring sultam derivatives by Michael addition and Baylis-Hillman reactions
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Five- and seven-membered sultam derivatives were conveniently synthesized via intra- or intermolecular Michael additions and an improved vinyl sulfonamide Baylis-Hillman reaction. Two different cyclization pathways were explored for the oxa-Michael reaction. A good solvent was discovered for an otherwise sluggish ketone-type Baylis-Hillman reaction in which vinyl sulfonamide ketones were used as the precursors. Furthermore, a strong base caused vinyl sulfonamide ketones to undergo 5-endo-trig intramolecular cyclizations, which are disfavored according to Baldwin's rule. Finally Baylis-Hillman reaction products were used as scaffolds for diversity-oriented sultam syntheses.
- Tong, Kun,Tu, Jinchang,Qi, Xueyong,Wang, Min,Wang, Yanjie,Fu, Haizhen,Pittman Jr., Charles U.,Zhou, Aihua
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supporting information
p. 2369 - 2375
(2013/03/29)
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- Cyclohexylamines
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The present application provides novel compounds and methods for preparing and using these compounds. These compounds are useful in treating pain, itch, overactive bladder and/or interstitial cystitis in patients by administering one or more of the compounds to a patient. The methods include administering a compound of formula (I) and a TRPV1 receptor activator. In one embodiment, the TRPV1 receptor activator is lidocaine.
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Paragraph 0217
(2013/05/08)
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- AROMATIC OXYPHENYL AND AROMATIC SYLFANYLPHENYL DERIVATIVES
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The present invention relates to compounds of formula I wherein the substituents are as defined below. The compounds of formula I are useful for the treatment of diseases such as schizophrenia, including both the positive and the negative symptoms of schizophrenia and other psychoses.
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- Reductive Alkylation of β-Alkanolamines with Carbonyl Compounds and Sodium Borohydride
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A synthesis of secondary alkylalkanolamines from primary alkanolamines in a rapid process in which overalkylation is virtually suppressed is described.The procedure combines the ease of formation of oxazolidines from alkanolamines with aldehydes or ketones in absolute ethanol and the lability of the newly formed C-O bond toward sodium borohydrode.The entire process is carried out in 15-35 min depending on the carbonyl substrate.
- Saavedra, Joseph E.
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p. 2271 - 2273
(2007/10/02)
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