- Synthesis and Antimicrobial Evaluation of Fire Ant Venom Alkaloid Based 2-Methyl-6-alkyl-Δ1,6-piperideines
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The first synthesis of 2-methyl-6-pentadecyl-Δ1,6-piperideine (1), a major alkaloid of the piperideine chemotype in fire ant venoms, and its analogues, 2-methyl-6-tetradecyl-Δ1,6-piperideine (2) and 2-methyl-6-hexadecyl-Δ1,6-piperideine (3), was achieved by a facile synthetic method starting with glutaric acid (4) and urea (5). Compound 1 showed in vitro antifungal activity against Cryptococcus neoformans and Candida albicans with IC50 values of 6.6 and 12.4 μg/mL, respectively, and antibacterial activity against vancomycin-resistant Enterococcus faecium with an IC50 value of 19.4 μg/mL, while compounds 2 and 3 were less active against these pathogens. All three compounds strongly inhibited the parasites Leishmania donovani promastigotes and Trypanosoma brucei with IC50 values in the range of 5.0-6.7 and 2.7-4.0 μg/mL, respectively.
- Yan, Yujie,An, Yu,Wang, Xiaozhong,Chen, Yingqi,Jacob, Melissa R.,Tekwani, Babu L.,Dai, Liyan,Li, Xing-Cong
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- The synthesis of unsubstituted cyclic imides using hydroxylamine under microwave irradiation
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Unsubstituted cyclic imides were synthesized from a series of cyclic anhydrides, hydroxylamine hydrochloride (NH2OH·HCl), and 4-N,N-dimethylamino-pyridine (DMAP, base catalyst) under microwave irradiation in monomode and multimode microwaves. This novel microwave synthesis produced high yields of the unsubstituted cyclic imides for both the monomode (61-81%) and multimode (84-97%) microwaves.
- Benjamin, Ellis,Hijji, Yousef
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Read Online
- Preparation method of glutaryl imide derivative
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The invention discloses a preparation method of a glutaryl imide derivative, which comprises the following steps: in a negative pressure state, dropwise adding acetic anhydride into molten 1, 1-cyclohexyl diacetic acid, and reacting to obtain 1, 1-cyclohexyl diacetic anhydride; adding ammonia water into an ammoniation kettle, dropwise adding 1, 1-cyclohexanediacetic anhydride to carry out ammoniation reaction, and adding hydrochloric acid to adjust the pH value, so as to obtain precipitated crystals, namely pentane valeric acid; adding pentane valeric acid, a toluene solvent and glacial aceticacid into the reaction kettle, heating, stirring, reacting, cooling, and carrying out suction filtration to obtain a filter cake; and adding the filter cake into ammonia water for soaking and stirring, carrying out suction filtration again, leaching with deionized water, and drying to obtain glutaryl imide. According to the preparation method of a glutaryl imide derivative, acetic anhydride and 1, 1-cyclohexyldiacetic acid are used as raw materials, so that the reaction efficiency is effectively improved, the product yield is increased, the production cost of the product is reduced, and producing benefits are improved.
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Paragraph 0037; 0041-0044; 0048-0051; 0053-0057
(2021/03/31)
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- Synthesis of N-unsubstituted cyclic imides from anhydride with urea in deep eutectic solvent (DES) choline chloride/urea
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N-Unsubstituted cyclic imides were readily synthesized in deep eutectic solvent (DES) choline chloride (ChCl)/urea from anhydrides with urea. Urea serves as both a DES component and a nitrogen source, which endows the protocol with advantages of smooth reaction, easy separation of products, simple recovery and recycling of ChCl/urea.
- Liu, Luxiao,Zhang, Hong-Yu,Yin, Guohui,Zhang, Yuecheng,Zhao, Jiquan
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p. 1351 - 1357
(2019/11/19)
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- Method for catalytically oxidizing amine to be synthesized into amide through dipyridyl-type manganese catalyst
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The invention discloses a methodfor catalytically oxidizing amine to be synthesized into amide througha dipyridyl-type manganese catalyst. According to the method, a dipyridyl manganese complex formedafter coordination of a dipyridyl-type complex and cheap metal manganese serves as the catalyst, clean and environment-friendly hydrogen peroxide serves as an oxidizing agent, oxidation of N ortho-position sp3 C-H bonds catalyzed by the cheap metal manganese is achieved, and the amine is directly oxidized to obtain the amide. Compared with existing methods, the method has the advantages that theadopted catalyst is low in price, the preparing method is simple, raw materials are easy to obtain, the use level of the catalyst is low, the substrate range is wide, the reaction condition is mild, the operation is simple and environmentally friendly, the reaction time is short, the yield is high, the selectivity is high, and the industrialization cost is low.
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Paragraph 0017-0027
(2019/06/30)
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- Visible-Light-Driven Oxidation of N -Alkylamides to Imides Using Oxone/H 2 O and Catalytic KBr
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Imides are prepared conveniently by visible-light-driven oxidations of various N -alkylamides under mild conditions. The majority of the reactions proceed efficiently by using Oxone as the oxidant in the presence of a catalytic amount of KBr in H 2 O/CH 2 Cl 2 under irradiation by an 8 W white LED at room temperature. Experimental studies suggest that an imine, obtained from the substrate amide via a radical process, is the key intermediate.
- Mei, Chong,Hu, Yixin,Lu, Wenjun
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p. 2999 - 3005
(2018/05/25)
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- Heterolytic (2 e) vs Homolytic (1 e) Oxidation Reactivity: N?H versus C?H Switch in the Oxidation of Lactams by Dioxirans
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Dioxiranes are powerful oxidants that can act via two different mechanisms: 1) homolytic (H abstraction and oxygen rebound) and 2) heterolytic (electrophilic oxidation). So far, it has been reported that the nature of the substrate dictates the reaction mode independently from the dioxirane employed. Herein, we report an unprecedented case in which the nature of the dioxirane rules the oxidation chemoselectivity. In particular, a switch from C?H to N?H oxidation is observed in the oxidation of lactams moving from dimethyl dioxirane (DDO) to methyl(trifluoromethyl)dioxirane (TFDO). A physical organic chemistry study, which combines the oxidation with two other dioxiranes methyl(fluoromethyl)dioxirane, MFDO, and methyl(difluoromethyl)dioxirane, DFDO, with computational studies, points to a diverse ability of the dioxiranes to either stabilize the homo or the heterolytic pathway.
- Annese, Cosimo,D'Accolti, Lucia,Fusco, Caterina,Licini, Giulia,Zonta, Cristiano
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supporting information
p. 259 - 262
(2017/01/17)
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- Strong influence of intramolecular Si?O proximity on reactivity: Systematic molecular structure, solvolysis, and mechanistic study of cyclic N-trimethylsilyl carboxamide derivatives
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A comparative alcoholysis study of N-silylated derivatives of simple heterocyclic carboxamides (lactams, imides, ureas) is presented. The second-order rate constant values span a range as wide as three orders of magnitude. On the basis of DFT calculations, a good correlation between reactivity and the Si?O distance was found within each family of compounds. The viability of two different reaction pathways was evaluated using a detailed computational mechanistic study of the methanolysis of cyclic urea homologues. Peculiarities in the single-crystal X-ray diffraction structures of the trimethylsilyl and trimethylsiloxy phthalimides are also discussed.
- Szalay, Roland,Harmat, Veronika,E?ri, János,Pongor, Gábor
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p. 2186 - 2192
(2017/05/16)
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- Nitrile synthesis through catalyzed cascades involving acid-nitrile exchange
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Irreversible acid-nitrile exchange reactions using both glutaronitrile and (phenylsulfonyl)acetonitrile may be catalyzed by Lewis acids. Whereas a cyclization towards imides displaces the equilibria in the reaction with dinitriles, a decarboxylation step is involved when using the (phenylsulfonyl)acetonitrile. Georg Thieme Verlag Stuttgart New York.
- Cartigny, Damien,Dos Santos, Aurelie,El Kaim, Laurent,Grimaud, Laurence,Jacquot, Roland,Marion, Philippe
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p. 1802 - 1806
(2014/07/08)
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- Method for producing compounds comprising nitrile functions
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The present invention concerns the production of compounds comprising nitrite functions and cyclic imide compounds. More specifically, the invention relates to the production of compounds comprising nitrile functions from compounds comprising carboxylic functions, advantageously of natural and renewable origin, and from methyl-2 glutaronitrile (MGN) or a mixture N of dinitriles comprising methyl-2 glutaronitrile (MGN), ethyl-2 succinonitrile (ESN) and adiponitrile (AdN).
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Paragraph 0071-0075; 0077-0078
(2014/12/09)
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- PROCESS FOR THE PREPARATION OF IMIDES AND DERIVATIVES THEREOF AND USES
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A process for the preparation of imides and also the uses thereof, especially as intermediates for the preparation of solvents, in particular of diester solvents, is described. Further described is a process for preparing cyclic imides and derivatives thereof, especially the corresponding carboxylic acids.
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Paragraph 0162-0164
(2014/01/08)
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- Oxidative cleavage of lactams in water using dioxiranes: An expedient and environmentally-safe route to ω-nitro acids
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By taking advantage of the appreciable stability of dioxiranes in water, a safe yet efficient route to ω-nitro acids by oxidation of lactams of various ring sizes under mild conditions has been reported. In essentially all the cases examined, reactions proceed selectively to afford products in remarkably high yields (up to 99%) and with high purity (94-99%). Also, an interesting example of higher reaction selectivity in water than in organic solvent (acetonitrile) is discussed.
- Annese, Cosimo,D'Accolti, Lucia,Filardi, Rosella,Tommasi, Immacolata,Fusco, Caterina
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p. 515 - 517
(2013/02/23)
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- AMIDOALKYLPIPERAZINYL DERIVATIVES FOR THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISEASES
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The invention relates to novel amidoalkylpiperazinyl derivatives of tricyclic heterocyclic systems of general formula (I), wherein Z represents -NH- and X represents -S-, or Z represents -S- and X represents >C=C1 represents H or -CH3, R6 and R7 both represent H, n is an integer from 0 to 4 inclusive, G represents a cyclic amide or imide moiety, and optical isomers, geometric isomers, and pharmaceutically acceptable salts thereof. The compounds may be useful for the treatment and/or prevention of the central nervous system disorders.
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Page/Page column 28; 29
(2013/03/26)
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- A mild and facile synthesis of cyclic imides using pyridinium chlorochromate
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A mild and facile synthetic method of cyclic imides is presented. These compounds are widely used in the synthesis of novel medical, polymeric, photonic and electronic materials. Compared with traditional syntheses, the method reported has several advantages including mild conditions, simplified work-up and low cost.
- Yang, Yanyan,Wang, Ge,Cao, Xiaohui,Yan, Xilong,Chen, Ligong
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p. 657 - 658,2
(2020/07/30)
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- Copper-catalyzed oxidative desulfurization-oxygenation of thiocarbonyl compounds using molecular oxygen: An efficient method for the preparation of oxygen isotopically labeled carbonyl compounds
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A novel copper-catalyzed oxidative desulfurization reaction of thiocarbonyl compounds, using molecular oxygen as an oxidant and leading to formation of carbonyl compounds, has been developed, and the utility of the process is demonstrated by its application to the preparation of a carbonyl-18O labeled sialic acid derivative. The Royal Society of Chemistry.
- Shibahara, Fumitoshi,Suenami, Aiko,Yoshida, Atsunori,Murai, Toshiaki
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p. 2354 - 2356
(2008/02/09)
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- Efficient tandem process for the catalytic deprotection of N-allyl amides and lactams in aqueous media: A novel application of the bis(allyl)- ruthenium(IV) catalysts [Ru(η3:η2: η3-C12H18)Cl2] and [Ru(η3:η3-C10H16)-(μ-Cl) Cl}2]
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An operationally simple and highly efficient methodology for the removal of the allyl protecting group in amides and lactams has been developed by using the commercially available bis(allyl)-ruthenium(IV) catalysts [Ru(η3:η2:η3-C12H 18)Cl2] (C12H18 = dodeca-2,6,10-triene-1,12-diyl) and [(Ru(η3:η3- C10H16)(μ-Cl)Cl}2] (C10H 16 = 2,7-dimethylocta-2,6-diene-1,8-diyl). The tandem process, which takes place in aqueous media and proceeds in a one-pot manner, involves the initial isomerization of the C=C bond of the allyl unit and subsequent oxidative cleavage of the resulting enamide.
- Cadierno, Victorio,Gimeno, Jose,Nebra, Noel
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p. 6590 - 6594
(2008/03/13)
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- Formamide, a novel challenging reagent for the direct synthesis of non-N-substituted cyclic imides
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Aliphatic and aromatic cyclic imides have been prepared in high to moderate yields from cyclic carboxylic anhydrides or corresponding dicarboxylic acids, using formamide as reagent at 170-180°C for 5-6 hours. In the case of aromatic products with lower solubility in formamide, we used N-methyl-2-pyrrolidinone (NMP) as supplementary solvent, which facilitates the reaction.
- Chiriac, Constantin I.,Nechifor, Marioara,Tanasǎ, Fulga
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p. 883 - 886
(2008/09/20)
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- Efficient microwave assisted syntheses of unsubstituted cyclic imides
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A number of cyclic imides were synthesized from cyclic anhydrides using ammonium chloride (NH4Cl), and 4-N,N-dimethylaminopyridine (DMAP) or with ammonium acetate (NH4OAc) under microwave irradiation in both a mono-mode and a conventional microwave. Several substituted succinic anhydrides used as reactants were synthesized efficiently by Diels-Alder reactions of maleic anhydride with 1,3-cyclohexadienes in 63-82% for the mono-mode and 72-92% in the conventional microwave ovens. Cyclic imides were synthesized with yields from 50-98%.
- Hijji, Yousef M.,Benjamin, Ellis
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p. 2259 - 2267
(2007/10/03)
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- Chemical and microsomal oxidation of tertiary amides: Regio- and stereoselective aspects
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The conformationally restricted tertiary amides N-methyl-2-pyrrolidone 6, N-methyl-2-piperidone 7 and N-methyl-ε-caprolactam 8 were oxidised by 5,10,15,20-tetraphenylporphyrinatoiron(III) chloride/tert-butyl hydroperoxide (TPPFe/ButOOH) and by phenobarbital-induced rat liver microsomes. The products were the N-demethylated lactams together with the analogous N-methylimides and norimides. For the TPPFe/ButOOH reaction ring oxidation is preferred to N-demethylation, paralleling the relative stabilities of the corresponding intermediate carbon-centred radicals as calculated by the AM1 semi-empirical method. In contrast, the microsomal reaction of the N-methyllactams strongly favours N-demethylation, demonstrating that hydrogen atom abstraction from the alkyl group Z to the amide carbonyl oxygen atom is preferred. The chiral tertiary amides N-methyl-N-(1-phenylethyl)benzamide 9 and N-methyl-5-phenyl-2-pyrrolidone 10 were also oxidised by TPPFe/ButOOH and by phenobarbital-induced rat liver microsomes. Using TPPFe/ButOOH, loss of the secondary alkyl group of 9 is preferred by a factor of ca. 6. Similarly, ring oxidation of 10 is favoured over demethylation by a factor of 9. For the microsomal reaction of (R)-9 dealkylation is preferred over demethylation by a factor of 1.7, whereas for (S)-9 demethylation is favoured by a factor of 1.25. For the microsomal reaction of (R)-10 and (S)-10 ring oxidation at the 5-position of the pyrrolidone ring is preferred over demethylation by factors of ca. 4 and 9 for the two isomers, respectively, and the (S)-enantiomer undergoes ring oxidation 2-3 times more readily than the (R)-enantiomer. For both 9 and 10 there is negligible stereochemical influence of the chiral centre upon the N-demethylation reaction. The results show that the stereochemical preference of the microsomal N-dealkylation reaction is modest.
- Iley, Jim,Tolando, Roberto,Constantino, Luis
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p. 1299 - 1305
(2007/10/03)
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- The return of the succinimidyl radical
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The aqueous kinetics of the succinimidyl radical, S., has been re-examined in the presence of oxidizable substrates and oxygen. The results indicate a rapid equilibrium between S. and its ring-opened analogue, the β-(isocyanato-carbonyl)ethyl radical, PI.. The equilibrium constant K1 is ca. 10, with k1 ≈ 107 s-1 and k-1 ≈ 106 s-1. The glutarimidyl radical, G., was produced by one-electron reduction of N-chloroglutarimide, GCl. The rate constants of several oxidation and hydrogen abstraction reactions with S. and G. have been determined. Furthermore, halogen abstraction reactions from haloimides by some selected alkyl radicals were also scrutinised. Most striking is the finding that the 2-cyanoethyl radical abstracts Br from SBr ca. 25 times slower than does the ethyl radical. This demonstrates a strong β-effect and rationalises a relatively slow Br abstraction rate by PI. from SBr. While the closure rate of the PI' radical appears to be solvent-insensitive, the ring opening rate of S., k1, is estimated to be ca. 100 times faster in, e.g., CH2Cl2 than in water. This suggests hydrogen-bonded stabilisation of S.. Acta Chemica Scandinavica 1998.
- Merenyi, Gabor,Lind, Johan,Eberson, Lennart
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- Anti-picornaviral agents
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The present invention provides a group of novel compounds that inhibit the proteolytic activity of 3C proteases which are found in picornaviruses, particularly rhinoviruses. In picornaviruses the RNA genome is translated into a single large viral polyprotein precursor. The precursor demonstrates auto-proteolytic activity, cleaving itself into mature viral gene products. Therefore, compounds of the current invention are particularly useful in treating picornaviral infections by interrupting the processing of the viral gene products into mature and infectious viral particles. The current invention also provides a novel process the preparation of compounds of the current invention. The process entails the selective reduction of an imide intermediate representing a marked improvement over processes known in the art for making peptidyl-aldehydes.
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- Herbicidal glutarimides
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This invention relates to glutarimide compounds exhibiting herbicidal activity having the structure STR1 wherein A is carbonyl, thiocarbonyl or methylene, A1 is carbonyl or methylene, Q is O or (CH2)n where n is 0 or 1, D is CH or N and R, R1, R2, T, X, Y and Z are as defined within, compositions containing these compounds and methods of using these compounds as herbicides and algicides.
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- Herbicidal glutaramic acids and derivatives
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This invention relates to glutaramic acids and derivatives exhibiting herbicidal activity having the structure STR1 wherein A is a carboxylic acid or a derivative thereof, D is CH or N, and R, R1, R2, T, X, Y, and Z are as defined within, compositions containing these compounds and methods of controlling weeds with these compounds.
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- SYNTHESIS OF 4-SUBSTITUTED GLUTARIMIDES BY FREE RADICAL ADDITION OF IODOACETAMIDE TO α,β-UNSATURATED ESTERS
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Free radical addition of either methyl bromoacetate or iodoacetamide to an α,β-unsaturated ester gave the 4-substituted glutarate or glutarimide respectively, whereas the radical cyclisation of N-bromoacetyl crotonamide gave the 2-substituted succinimide.
- Sacripante, Guerino,Tan, Charles,Just, George
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p. 5643 - 5646
(2007/10/02)
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- Synthesis of Diazaheterocycles with a Bridgehead Nitrogen by Photocyclization of N-Substituted Alicyclic Imides
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N-(Dialkylaminomethyl)-succinimides or - glutarimides give 1,3-diazabicyclooctanes or --nonanes on irradiation in acetonitrile, accompanied by variable amounts of the parent imide.Two diastereomers of the products can be pbtained, and the relative stereochemistry assigned on the basis of n.m.r. data.With unsymmetrical substrates mixture of products are formed that demonstrate orientational preferences.Analogous N-substituted pyrrolidin-2-ones do not give photocyclised products (an unusual cleavage product is isolated in low yield), and similar dihydrouracils are relatively photostable.N-(Dialkylaminoethyl) aliphatic imides give azepine- or azocine-diones on irradiation, whereas N-(dialkylaminopropyl) compounds undergo photocyclisation to products with a new perhydro-1,4-diazepine ring (as do a corresponding 3,4,5,6-tetrahydrophthalimide and phthalimide, although photoreduction is a major process for the latter system).An N-(dialkylaminobutyl)succinimide does not give products with a new perhydrodiazocine ring.An N-(dialkylaminoethyl)maleimide and the analogous 3,4,5,6-tetrahydrophthalimide give compounds that contain a new piperazine ring, which is in contrast to the saturated imide analogues but similar to the corresponding phthalimide; this process competes effectively with the more usual photoreactions of maleimides involving the carbon-carbon double bond.
- Coyle, John D.,Bryant, Laurence, R. B.
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p. 2857 - 2865
(2007/10/02)
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- PREPARATION OF SEVERAL NEW Ni- OR Pd-CONTAINING CYCLIC AMIDE AND ESTERS, (PR3)nNi(CH2CH2CH2COZ) (Z=NH, O) AND PCy3Pd(CH2CH2CH2COO), AND RING CONTRACTION OF THE SIX-MEMBERED Ni-CONTAINING CYCLIC ESTER TO ITS FIVE-MEMBERED ISOMER
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New metallacyclic amide and esters (PCy3Ni(CH2CH2CH2CONH), (PR3)nNi(CH2CH2CH2COO), PCy3Pd(CH2CH2CH2COO) ) have been prepared by reactions of zero-valent nickel and palladium complexes with unsaturated amide and acid.The 6-membered Ni-containing cyclic ester undergoes a ring contraction reaction to a 5-membered isomer.
- Sano, Kenji,Yamamoto, Takakazu,Yamamoto, Akio
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p. 695 - 698
(2007/10/02)
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- Structure and Stereochemistry of Lactams and Cyclic Imides. V. Mass Spectrometry of Substituted Glutarimides
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Fragmentation pathways of cyclic imides based on high resolution MS measurements of six mono-, di- and trimethyl glutarimides are proposed.They can be treated as general ones.Most of integral ions have been found to consist of two different ones, which was not observed before.Relationship between the structures and abundances of several integral ions derived from substituted glutarimides has been observed.
- Dabrowski, Zbigniew,Cybulski, Jacek
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