- Effect of the Leaving Group in the Hydrolysis of N-Acylimidazoles. The Hydroxide Ion, Water, and General Base Catalyzed Hydrolysis of N-Acyl-4(5)-nitroimidazoles
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The second-order rate constants kOH for hydroxide ion catalyzed hydrolysis of N-acylimidazoles substituted in the imidazole group show only a moderate dependence on the pKa of the leaving group (βlg = -0.28), which indicat
- Fife, Thomas H.,Natarajan, R.,Werner, Milton H.
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Read Online
- An efficient catalytic method for the c-n acylation of heterocycles by schiff base co(Ii), ni(ii), cu(ii) and zn(ii) transition metal complexes
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The catalytic activity of Schiff base Co(II), Ni(II), Cu(II) and Zn(II) transition metal complexes was tested for N-Acylation of heterocycles with acetyl chloride. It is observed that all the complexes worked as efficient catalysts. The structural type of complexes was studied by an X-ray powder diffractogram (XRD). The mixed ligand complexes with PPh3 ligand show greater activity as compared to Phen complexes and Schiff base complexes. Especially complex [Ni(L)(PPh3)2Cl2] efficiently worked as a catalyst because of high thermal stability (TGA-DSC) and large catalytic surface area (BET).
- Hegade, Sujit,Gaikwad, Gautam,Jadhav, Yuvraj,Chavan, Sanjay,Mulik, Ganpatrao
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p. 611 - 616
(2021/09/30)
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- N-Acylazole mediated stereoselective and regioselective synthesis of N-substituted azole acrylonitriles
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Regio- and stereoselective synthesis of N -substituted azole acrylonitriles has been achieved smoothly in N, N -dimethylformamide (DMF) in the presence of potassium carbonate (K 2 CO 3) as a base catalyst. N -Substituted azole acrylonitriles were obtained
- Aydin, Osman,K?kten, ?ule,ünver, Hakan,?elik, ?lhami
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p. 1134 - 1148
(2019/09/10)
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- Synthesis of Some Benzimidazole-based Heterocycles and their Application as Copper Corrosion Inhibitors
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A series of new substituted benzimidazoles embedded with a variety of function groups has been synthesized from N-methyl-2-bromoacetylbenzimidazole. The synthesized compounds were fully characterized, and their structures were elucidated based on elemental analysis, spectral data, and alternative synthetic pathways, whenever possible. Some of benzimidazole derivatives were tested as corrosion inhibitors.
- Eldebss, Taha M. A.,Farag, Ahmad M.,Shamy, Adel Y. M.
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p. 371 - 390
(2019/01/08)
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- A azole amide preparation method of the compound
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A preparation method of an azole-series amide compound. The invention discloses a method including a reaction that the azole-series amide is synthesized from a carboxylic acid compound and an azole compound with a copper salt as a catalyst and molecular o
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Paragraph 0019-0021; 0025-0027; 0065-0066
(2018/04/27)
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- Facile One-Pot Synthesis of Benzimidazole and Quinoxalin-2(1 H)-one Scaffolds via Two-Component Coupling Reaction, Deprotection, and Intermolecular Cyclization
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Two scaffolds, namely benzimidazole and quinoxalin-2(1H)-one, were synthesized by treating 2-(N-Boc-amino)phenylisocyanide (Boc: tert-butoxycarbonyl) with carboxylic acids and glyoxylic acids, respectively. The target compounds were generated directly aft
- Chen, Zhong-Zhu,Tang, Ying,Zuo, Lei,Tang, Dian-Yong,Zhang, Jin,Xu, Zhi-Gang
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supporting information
p. 2518 - 2520
(2015/07/27)
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- Solvent free, highly chemoselective N and O-acylation on silica and silica magnesium oxide: A recyclable solid surface
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Silica or silica/magnesium oxide mixed surface mediates the N and O-acylation, benzoylation or sulfonylation of hosts of substrates under solvent free conditions at ambient temperature with high chemoselectivity.
- Ghosh, Pranab,Mandal, Amitava
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p. 261 - 268
(2012/10/29)
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- Inhibitors of the salicylate synthase (Mbti) from Mycobacterium tuberculosis discovered by high-throughput screening
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A simple steady-state kinetic high-throughput assay was developed for the salicylate synthase MbtI from Mycobacterium tuberculosis, which catalyzes the first committed step of mycobactin biosynthesis. The mycobactins are small-molecule iron chelators produced by M. tuberculosis, and their biosynthesis has been identified as a promising target for the development of new antitubercular agents. The assay was miniaturized to a 384-well plate format and high-throughput screening was performed at the National Screening Laboratory for the Regional Centers of Excellence in Biodefense and Emerging Infectious Diseases (NSRB). Three classes of compounds were identified comprising the benzisothiazolones (class I), diarylsulfones (class II), and benzimidazole-2-thiones (class III). Each of these compound series was further pursued to investigate their biochemical mechanism and structure-activity relationships. Benzimidazole-2-thione 4 emerged as the most promising inhibitor owing to its potent reversible inhibition.
- Vasan, Mahalakshmi,Neres, Joao,Williams, Jessica,Wilson, Daniel J.,Teitelbaum, Aaron M.,Remmel, Rory P.,Aldrich, Courtney C.
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experimental part
p. 2079 - 2087
(2011/11/29)
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- Synthesis of analogs of L-valacyclovir and determination of their substrate activity for the oligopeptide transporter in Caco-2 cells
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L-Valacyclovir, a prodrug of acyclovir, is a substrate for the peptide transporter (PepT1) in the intestinal mucosa, which accounts for its higher than expected oral bioavailability. The substrate activity of L-valacyclovir for PepT1 is surprising, particularly when one considers that the molecule has the structural features of a nucleoside rather than a peptide. In an attempt to better understand the structure-transport relationships (STR) for the interactions of L-valacyclovir with PepT1, analogs of this molecule with structural changes in the guanine moiety were synthesized and their substrate activity for PepT1 in Caco-2 cell monolayers was determined. The analogs synthesized include those that had the guanine moiety of L-valacyclovir substituted with purine, benzimidazole, and 7-azaindole. All three analogs (purine, benzimidazole, and 7-azaindole) exhibited affinity for PepT1 in binding studies, but only the purine analog (as the L-valine ester) showed PepT1-associated transcellular transport across Caco-2 cell monolayers. The benzimidazole and 7-azaindole analogs (as their L-valine esters) were rapidly metabolized by esterase when applied to the apical surface of Caco-2 cells, which probably explains their low penetration as the intact prodrugs via PepT1.
- Friedrichsen, Gerda Marie,Chen, Weiqing,Begtrup, Mikael,Lee, Chao-Pin,Smith, Philip L.,Borchardt, Ronald T.
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- An efficient synthesis of mimetics of neamine for RNA recognition.
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As mimetics of neamine, several 4-heterocyclic 2-deoxystreptamine derivatives were chemically synthesized for RNA recognition. Conversion of 4-methylthiomethyl-5,6-di-O-acetyl-diazido-2-deoxystreptamine to the 4-chloromethyl derivative followed by reactions with different nuclophilic reagents gave the 4-heterocyclic 2-deoxystreptamine derivatives in satisfactory yields.
- Ding,Hofstadler,Swayze,Griffey
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p. 1621 - 1623
(2007/10/03)
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- Studies on synthesis of 2-acetylbenzimidazole and related benzimidazole derivatives
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Condensation of o-phenylenediamine (1) with propanoic acid under Phillips' conditions gives 2-ethylbenzimidazole (2). Attempts to oxidise 2 to 2-acetylbenzimidazole (3) using H2O2, SeO2, KMnO4/acetone were unsuccessful. Condensation of 2 with benzaldehyde yields 2-(α-methylstyryl)benzimidazole (4) which on oxidation with KMnO4 gives benzimidazole-2-carboxylic acid (5) as the sole product. Reaction of 1 with pyruvic acid results in 3-methylbenzo-1H-dihydropyrazine-2-one (7) rather than 3 as the major product. Treatment of 1 with formic acid gives the known compound benzimidazole (9) which with acetic anhydride in the presence of NaOAc does not yield 3. Reaction of 1 with lactic acid under Phillips' conditions gives 2-(α-hydroxyethyl)benzimidazole (10) which on oxidation with acid dichromate, however, yields 3. Studies on syntheses and spectral properties of related benzimidazoles are reported.
- Ramaiah,Grossert,Hooper,Dubey,Ramanatham
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p. 140 - 144
(2007/10/03)
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- N-Cyanazoles in Synthesis of Amides of Carboxylic Acids
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The reaction of carboxylic acids with 1-cyanimidazole, 1-cyanobenzimidazole, and 1-cyano-1,2,4-triazole leads to the formation of 1-acylazoles used in situ in synthesis of anilides of the corresponding carboxylic acids.
- Purygin,Pan'kov
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p. 871 - 873
(2007/10/03)
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- OXIDATION OF 1-AMINOBENZIMIDAZOLES. SYNTHESIS AND PROPERTIES OF 1,1'-AZOBENZIMIDAZOLES
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1-Amino-2-R-benzimidazoles are oxidized by lead tetraacetate to give, depending on the substituent in the 2-position, either to 1,1'-azobenzimidazoles (R=H, CH3, C6H5, Cl, N(CH3)2) or 3-R-benzo-1,2,4-triazines (R=NH2, NHCH3, NHC6H5, OH).The factors affecting the course of the reaction are discussed.The physicochemical properties of the 1,1'-azobenzimidazoles obtained have been examined.
- Pozharskii, A. F.,Nanavyan, I. M.,Kuz'menko, V. V.,Chernyshev, A. I.,Orlov, Yu. V.,Klyuev, N. A.
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p. 1241 - 1253
(2007/10/02)
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- Hydrolysis rates of some acetylimidazole derivatives
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N-Acetylbenzimidazole (4), N-acetyl-N'-methylbenzimidazolium acetate (5), and N-acetyl-N'-methyltetrahydrobenzimidazolinium acetate (6) were synthesized and their hydrolysis rate were studied.
- Gour-Salin, B. J.
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p. 2059 - 2061
(2007/10/02)
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