- A Convenient Protocol for the Synthesis of Fatty Acid Amides
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Several classes of biologically occurring fatty acid amides have been reported from mammalian and plant sources. Many amides conjugated with fatty acids of mammalian origin exhibit specific activation of individual receptors. Their potential as pharmacological tools or as lead compounds towards the development of novel therapeutics is of great interest. Hence, access to such amides by a practical, high-yielding and scalable protocol without affecting the geometry or position of sensitive functionalities is needed. A protocol that meets all these requirements involves activation of the corresponding acid with carbonyl diimidazole (CDI) followed by reaction with the desired amine or its hydrochloride. More than fifty compounds have been prepared in generally high yields.
- Johansson, Silje J. R.,Johannessen, Tonje,Ellefsen, Christiane F.,Ristun, Mali S.,Antonsen, Simen,Hansen, Trond V.,Stenstrom, Yngve,Nolsoe, Jens M. J.
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supporting information
p. 213 - 217
(2019/01/14)
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- Metal–Organic Framework Based on Copper and Carboxylate-Imidazole as Robust and Effective Catalyst in the Oxidative Amidation of Carboxylic Acids and Formamides
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A metal–organic framework (MOF) based on copper and 1,3-bis(carboxymethyl)imidazole (bcmim) was prepared on a gram scale by using a precipitation method at room temperature. The Cu(bcmim)2MOF was shown to be an efficient catalyst for the preparation of amides through an oxidative coupling between carboxylic acids and formamides in the presence of an oxidant, such as tert-butyl hydroperoxide (TBHP). The method for the preparation of the amides is robust regardless of the carboxylic acid and gives good conversions with good selectivity. The heterogeneous catalyst was recovered unaltered after the reaction, was easily separated from the reaction mixture, and subsequently reactivated by suitable treatment. Moreover, the coupling reaction was scaled up to a gram scale, which allowed for the preparation of valuable products, such as fatty acid amides (i.e., 1-palmitoylpiperidine).
- Albert-Soriano, María,Pastor, Isidro M.
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supporting information
p. 5180 - 5188
(2016/10/26)
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- A novel aromatic carbocation-based coupling reagent for esterification and amidation reactions
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A novel tropylium-based coupling reagent has been developed to facilitate the synthesis of a series of esters, amides, lactones and peptides under mild reaction conditions. Remarkably, this reagent can be used in catalytic amounts in conjunction with a sacrificial reagent, offering a new and efficient method for nucleophilic coupling reactions of carboxylic acids.
- Nguyen, Thanh V.,Lyons, Demelza J.M.
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supporting information
p. 3131 - 3134
(2015/06/17)
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- GC/MS investigations of the minor constituents of Piper guineense stem
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Chemical investigations by GC/MS-analysis of stem extracts of Piper guineense resulted in the detection and identification of thirty-nine new constituents of the stem, apart from previously isolated constituents. These are isobutyl, pyrrolidyl and piperidyl amide alkaloids. Fifteen new natural products have been identified. Four of these natural products have been designated iyeremide A and B (these are pyrrolidine and piperidine analogues of pellitorine) and cycloguineense A and B, which are also piperidine analogues of cyclostachine A and B. There is a need to confirm the structures of some of these new constituents by synthesis. Apart from these amide alkaloids, many volatile oil components-monoterpenes, sesquiterpenes, terpenoids, lignans and sterols - were detected.
- Adesina,Adebayo,Adesina,Groening
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p. 622 - 627
(2007/10/03)
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- Preparation and Characterization of 1,5-Diacyl-2,4-dioxohexahydro-1,3,5-triazines with Higher Acyl Groups
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The title compounds were prepared from 2,4-dioxohexahydro-triazine (DHT) and the corresponding acid chlorides in the presence of sulphuric acid.They are active acylating agents against piperidine in dioxane as the solvent.Only the diacyl derivatives of DHT with acyl chain lengths up to C6 react with aqueous solutions of sodium perborate forming the corresponding peroxy acids.
- Hofmann, Joerg,Just, Gerhard,Pritzkow, Wilhelm
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- Dermal penetration enhancement profile of hexamethylenelauramide and its homologues: In vitro versus in vivo behavior of enhancers in the penetration of hydrocortisone
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Several amides of cyclic amines were prepared and tested as penetration enhancers in the diffusion of various drugs through hairless mouse skin in vitro. Hexamethylenelauramide (hexahydro-1-lauroyl-1H-azepine) was selected as a broad spectrum penetration enhancer worthy of further study. Later, the duration of the effect of various enhancers on the penetration barrier in vivo was determined by evaluating the in vitro diffusion of hyrocortisone through skins that had been pretreated in vivo. We found that the longer the pretreatment, the smaller the amount of penetrated hydrocortisone. Furthermore, our results suggested that differences exist in the retention of various enhancers in living mouse skin. The in vitro pretreatment experiments revealed that the penetration through dead skin is slow compared with the penetration through living skin. Neither the nature of the receptor phase, nor the increased temperature of the in vitro experiments, explain the striking differences between the in vivo and the in vitro experiments. Finally, the penetration of hydrocortisone through the stratum corneum in the presence of enhancers, as well as the penetration of 1-dodecylhexahydro-2H-azepin-2-one (laurocapram), hexamethylenelauramide, and oleic acid, were determined using a stratum corneum stripping technique. More hydrocortisone penetrated through the stratum corneum during the first 3 h in the presence of hexamethylenelauramide than in the presence of laurocapram or oleic acid.
- Mirejovsky,Takruri
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p. 1089 - 1093
(2007/10/02)
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- HIGH CHEMOSELECTIE SYNTHESIS OF CARBOXAMIDES BY USING SYN-PHENYLPYRIDYL-O-ACYL OXIMES(PPKO)
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Various carboxamides are prepared chemoselectively in good yields by using syn-phenylpyridyl ketoxime(PPKO) as functional leaving group.
- Miyasaka, Tadayo,Noguchi, Shunsaku
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p. 701 - 704
(2007/10/02)
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- Monitored Aminolysis of 3-Acyl-1,3-thiazolidine-2-thiones: Synthesis of Amides and Amide Alkaloids
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A functional heterocycle, 3-acyl-1,3-thiazolidine-2-thione has been shown to be effective as an acylating reagent for the amino group.ATT (1) was readily prepared by several methods, and reacted with various amino compounds in CHCl3, CH2Cl2, THF, EtOH, THF-H2O, or sulfolane to afford the corresponding amides, 2a-w and 3-10 in very high yields within a short time.This reagent exhibits high chemo-selectivity.Its reaction with the diamines 13 and 15 and the triamine 29, which include a primary amino group(s) and a secondary amino group, gave the products acylated only at the primary amino group(s), 14, 16, and 30, respectively, in high yields.Aminoalcohols and aminophenols were chemoselectively converted into acylaminoalcohols and acylaminophenols, respectively, by ATT (1).By utilizing this method, several amide alkaloids (26, 28, 30, and 34) were efficiently synthesized.This new aminolysis can be monitored by the disappearance of the yellow color of the starting materials, ATT (1); it is remarkably characteristic of this reaction. Keywords - monitored aminolysis; 3-acyl-1,3-thiazolidine-2-thione; high chemo-selectivity; amide synthesis; fagaramide; dolicotheline; spermidine; maytenine; N-ferulyltryptamine
- Nagao, Yoshimitsu,Seno, Kaoru,Kawabata, Kohji,Miyasaka, Tadao,Takao, Sachiko,Fujita, Eiichi
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p. 2687 - 2699
(2007/10/02)
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- MONITORED AMINOLYSIS OF 3-ACYLTHIAZOLIDINE-2-THIONE : A NEW CONVENIENT SYNTHESIS OF AMIDE
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3-Acylthiazolidine-2-thiones (1) were easily prepared and they were treated with several amines in dichloromethane to give amides 4 in very high yields within a short time.Aminoalcohols and aminophenols were selectively converted into acylaminoalcohols and acylaminophenols, respectively, by this reaction.One can monitor the reaction by disappearance of the yellow color of the starting material 1.Some amide alkaloids (15-18) have effectively been synthesized.
- Nagao, Yoshimitsu,Seno, Kaoru,Kawabata, Kohji,Miyasaka, Tadayo,Takao, Sachiko,Fujita, Eiichi
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p. 841 - 844
(2007/10/02)
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