15510-09-5Relevant articles and documents
Nucleophilic Substitution at the Guanidine Carbon Center via Guanidine Cyclic Diimide Activation
An, Taeyang,Lee, Yan
supporting information, p. 9163 - 9167 (2021/11/24)
Despite the electron-deficient nature of the guanidine carbon centers, nucleophilic reactions at these sites have been underdeveloped because of the resonance stabilization of the guanidine group. We propose a guanidine C-N bond substitution strategy entailing the formation of guanidine cyclic diimide (GCDI) structures, which effectively destabilize the resonance structure of the guanidine group. In the presence of acid additives, the guanidine carbon center of GCDIs undergoes nucleophilic substitution reactions with various amines and alcohols.
Microwave-promoted direct amidation of unactivated esters catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions
Fu, Renzhong,Yang, Yang,Ma, Yunsheng,Yang, Fei,Li, Jingjing,Chai, Wen,Wang, Quan,Yuan, Rongxin
supporting information, p. 4527 - 4531 (2015/06/30)
Abstract A simple and efficient procedure for the synthesis of amides directly from unactivated esters and amines catalyzed by heteropolyanion-based ionic liquids under microwave-promoted and solvent-free conditions has been reported. The practical protocol was found to be compatible with different structurally diverse substrates. Moderate to excellent yields, solvent-free media, and operational simplicity are the main highlights. Furthermore, the heteropolyanion-based ionic liquids were easily reusable for this amidation.
One-pot mechanosynthesis of aromatic amides and dipeptides from carboxylic acids and amines
?trukil, Vjekoslav,Bartolec, Boris,Portada, Tomislav,Dilovi?, Ivica,Halasz, Ivan,Margeti?, Davor
supporting information, p. 12100 - 12102 (2013/01/16)
Environmentally friendly one-pot synthesis of amides, bis-amides and dipeptides by mechanochemical carbodiimide-mediated coupling of carboxylic acids and amines is described; high reaction yields and simple aqueous work-up allow for the clean, practical and fast preparation of a variety of compounds containing the amide bond from readily accessible reagents.
Simultaneous quantification of metabolites involved in central carbon and energy metabolism using reversed-phase liquid chromatography-mass spectrometry and in vitro 13C labeling
Yang, Wen-Chu,Sedlak, Miroslav,Regnier, Fred E.,Mosier, Nathan,Ho, Nancy,Adamec, Jiri
experimental part, p. 9508 - 9516 (2009/07/11)
Comprehensive analysis of intracellular metabolites is a critical component of elucidating cellular processes. Although the resolution and flexibility of reversed-phase liquid chromatography-mass spectrometry (RPLC-MS) makes it one of the most powerful analytical tools for metabolite analysis, the structural diversity of even the simplest metabolome provides a formidable analytical challenge. Here we describe a robust RPLC-MS method for identification and quantification of a diverse group of metabolites ranging from sugars, phosphosugars, and carboxylic acids to phosphocarboxylics acids, nucleotides, and coenzymes. This method is based on in vitro derivatization with a 13C-labeled tag that allows internal standard based quantification and enables separation of structural isomer pairs like glucose 6-phosphate and fructose 6-phosphate in a single chromatographic run. Calibration curves for individual metabolites showed linearity ranging over more than 2 orders of magnitude with correlation coefficients of R2 > 0.9975. The detection limits at a signalto-noise ratio of 3 were below 1.0 μM (20 pmol) for most compounds. Thirty common metabolites involved in glycolysis, the pentose phosphate pathway, and tricarboxylic acid cycle were identified and quantified from yeast lysate with a relative standard deviation of less than 10%.
Efficient microwave access to polysubstituted amidines from imidoylbenzotriazoles
Katritzky, Alan R.,Cai, Chunming,Singh, Sandeep K.
, p. 3375 - 3380 (2007/10/03)
Microwave reactions of primary and secondary amines with imidoylbenzotriazoles 6a-w gave diversely substituted amidines 7a-Aa in 76-94% yields. Convenient preparations of a variety of amides 5a-Ab (87-96%) and imidoylbenzotriazoles 6a-w (56-95%) have also been developed using microwave irradiation under mild conditions and short reaction times. These results demonstrate further the advantages of microwave synthesis and introduce a new application of imidoylbenzotriazoles in the preparation of polysubstituted amidines.
Synthesis of N,N′-diarylalkanediamides and their antimycobacterial and antialgal activity
Kubicova, Lenka,Waisser, Karel,Kunes, Jiri,Kralova, Katarina,Odlerova, Zelmira,Slosarek, Milan,Janota, Jiri,Svoboda, Zbynek
, p. 714 - 726 (2007/10/03)
A set of N,N′-diarylalkanediamides was synthesized. The compounds were tested for their antimycobacterial and antialgal activity. The antimycobacterial activity of N,N′-diarylalkanediamides depends on the lipophilicity of the respective acid. Antimycobacteri-ally active substances were found only in the series of N,N′-diarylethanediamides and N,N′-diarylbutanediamides. Other compounds (derivatives of pentane-, hexane-, octane- and nonanediamide) were inactive against various strains of mycobacteria. The compounds inhibited growth and chlorophyll production in Chlorella vulgaris. Their relatively low antial-gal activity is probably connected with their lowered aqueous solubility, and hence by a restricted passage of the inhibitor through the hydrophilic regions of thylakoid membranes.
Reaction of Phenyl Isothiocyanate with Some α,N-Acylamino and Dicarboxylic Acids
Ashare, Ram,Ram, Ram N.,Mukerjee, Arya K.
, p. 759 - 760 (2007/10/02)
Dianilides are obtained in the reaction of phenyl isothiocyanate with dicarboxylic acids, such as oxalic, malonic, glutaric and adipic acids, and not in the case of succinic and phthalic acids.In the case of succinic acid, the product is monoanilide, dianilide or N-phenylsuccinimide, depending upon the reaction conditions.Phthalic acid always gives N-phenylphthalimide.N-Acylamino acids on reaction with phenyl isothiocyanate yield the corresponding anilides.The probable mechanisms of this reaction are discussed.
Derivatives of 1,3,5-Triazine: Part III - Cyanuric Chloride-Dimethylformamide as a New Reagent for Synthesis of Amides, Esters, Aldehydes and for Dehydration Reactions
Lahoti, R. J.,Wagle, D. R.
, p. 1007 - 1008 (2007/10/02)
Cyanuric chloride reacts with dimethylformamide to form a complex (I), which can be used directly for the synthesis of amides, esters, relatively simple peptides, aldehydes and for dehydration reactions.
