- Antimicrobial and lubrication properties of 1-acetyl-3-hexylbenzotriazolium benzoate/sorbate ionic liquids
-
Ionic liquids exhibit immense potential for a wide range of applications including biotechnology, medicinal chemistry and lubrication. Herein, 1-acetyl-3-hexylbenzotriazolium cation-based ionic liquids having benzoate and sorbate anions are prepared by chemical derivatization of benzotriazole. The antimicrobial activities of these ionic liquids are studied using the Escherichia coli and Rhodococcus erythropolis bacterial cultures and we monitored their growth inhibition property. Further, the biostatic properties are evaluated by the kinetic growth rate inhibition method. These ionic liquids exhibited improved antimicrobial activities compared to their precursors: benzotriazole, sodium benzoate and potassium sorbate. Furthermore, these ionic liquids as an additive to polyol lube base oil improved the lubrication property by reducing the friction and wear characteristics. Microscopic images along with elemental mapping of worn surfaces confirmed the formation of an ionic liquid-constituted tribo-chemical thin film, which protects the contact surfaces against the undesirable wear and reduces the friction.
- Bakshi, Paramjeet Singh,Gusain, Rashi,Dhawaria, Manisha,Suman, Sunil K.,Khatri, Om P.
-
-
Read Online
- Fast, economic, and green synthesis of N-formylated benzotriazoles
-
Formylation is an integral part of organic, medicinal, and biological chemistry both in industrial and academic set-ups. A reflection of this importance is the number of approaches and reagents that have been developed to achieve it. We have developed a fast, efficient, and environmentally friendly procedure for the synthesis of N-formylated benzotriazoles.
- Pasqua, Adele E.,Matheson, Mhairi,Sewell, Alan L.,Marquez, Rodolfo
-
-
Read Online
- Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides
-
Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.
- Qu, Erdong,Li, Shangzhang,Bai, Jin,Zheng, Yan,Li, Wanfang
-
supporting information
p. 58 - 63
(2021/12/27)
-
- THERAPEUTIC COMPOUNDS AND METHODS
-
Disclosed herein are compounds of formula I: (I) or pharmaceutically acceptable salts thereof, wherein R1, R2, and R3 may any of the values defined herein, as well as compositions comprising such compounds. Also disclosed are methods for treating diseases including neurodegenerative disorders such as Parkinson's Disease and Alzheimer's Disease.
- -
-
Page/Page column 26; 27
(2020/01/31)
-
- Cu-catalyzed arylation of 1-acyl-1H-1,2,3-Benzotriazoles via C–N activation
-
An efficient copper-catalyzed arylation reaction of 1-acyl-1H-1,2,3-benzotriazoles with diaryliodonium salts via C–N activation is explored. The reaction is conducted regioselectively to form 1-aryl-1H-1,2,3-benzotriazoles in MeCN at 80 °C in the presence of cesium carbonate. 29 examples are given with the product yield of up to 84%. The probable reaction mechanism is proposed.
- Zhang, Wenying,Wang, Yangyang,Jia, Xiangru,Du, Zhengyin,Fu, Ying
-
supporting information
p. 64 - 67
(2019/06/10)
-
- N-Acylazole mediated stereoselective and regioselective synthesis of N-substituted azole acrylonitriles
-
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
-
p. 1134 - 1148
(2019/09/10)
-
- Substituent effects in solid-state assembly of activated benzotriazoles
-
Aromatic donor-acceptor stacking involving electron-rich π-donors and electron-deficient π-acceptors has been utilized in a broad spectrum of diverse applications to great effect. We report the discovery of unprecedented donor-acceptor stacking from a non
- Wenholz, Daniel S.,Bhadbhade, Mohan,Kandemir, Hakan,Ho, Junming,Kumar, Naresh,Black, David Stc.
-
p. 835 - 842
(2019/02/05)
-
- Identification of a novel class of quinoline-oxadiazole hybrids as anti-tuberculosis agents
-
A series of novel quinoline-oxadiazole hybrid compounds was designed based on stepwise rational modification of the lead molecules reported previously, in order to enhance bioactivity and improve druglikeness. The hybrid compounds synthesized were screened for biological activity against Mycobacterium tuberculosis H37Rv and for cytotoxicity in HepG2 cell line. Several of the hits exhibited good to excellent anti-tuberculosis activity and selectivity, especially compounds 12m, 12o and 12p, showed minimum inhibitory concentration values 500. The results of this study open up a promising avenue that may lead to the discovery of a new class of anti-tuberculosis agents.
- Jain, Puneet P.,Degani, Mariam S.,Raju, Archana,Anantram, Aarti,Seervi, Madhav,Sathaye, Sadhana,Ray, Muktikanta,Rajan
-
p. 645 - 649
(2016/01/09)
-
- Intramolecular communication and electrochemical observation of the 17-electron ruthenocenium cation in fluorinated ruthenocene-containing β-diketones; Polymorphism of C10H21 and C 10F21 derivatives
-
Ruthenocene-containing β-diketones, RcCOCH2COR with Rc = ruthenocenyl and R = C10F21 (1), CF3 (2), C6F5 (3), C10H21 (4), CH3 (5) and C6H5 (6), were synthesised by Claisen condensation of the appropriate methyl ester with acetylruthenocene, and their spectroscopic, electrochemical and thermal properties were compared. A new synthetic route utilising 1,2,3-benzotriazol-1-ylethanone (9) or 1,2,3-benzotriazol-1-yl(ruthenocenyl)methanone (10) as a reactant, rather than the conventional esters, was found to be more efficient for β-diketone synthesis. The apparent acid dissociation constants, pKa′, of the new ruthenocene-containing β-diketones are 7.14(4) (1, R = C 10F21), 9.92(3) (3, R = C6F5) and 10.06(2) (4, R = C10H21). Peak anodic potentials of the ruthenocenyl group of 1-6, pKa′ values and the FTIR ν(CO) stretching frequencies of the precursor esters, RCOOCH3, correlated linearly with the Gordy scale group electronegativity, χR, of the C10F21 (χC10F21 = 3.04), C 6F5 (χC6F5 = 2.46), C 10H21 (χC10H21 = 2.43) and other R-groups. An electrochemical study in the non-interacting solvent and electrolyte system CH2Cl2/0.1 mol dm-3 [N( nBu4)][B(C6F5)4] revealed electrochemically irreversible one-electron transfer Rc/Rc+ couples in the potential range 650 pa +(C 5H5)(C5H4COCH2COR)], was clearly observed for all β-diketones possessing fluorinated R-groups, even at slow (100 mV s-1) scan rates. The enol isomer of the fluorinated β-diketones had >90% abundance under the conditions of study and the first order rate constant of enol to keto conversion varied between 220 and 50 000 s-1 depending on solvent (CDCl3 or CD3CN) and R-groups. Thermal analysis (DSC) of 1 and 4 showed no liquid crystalline mesophase behaviour but definite polymorphism was observed. β-diketones 1 and 4 exist as low temperature polymorphs below 42°C or 12°C respectively. The high temperature polymorphs converted to isotropic liquids at 83°C (compound 1) or 52°C (compound 4).
- Erasmus, Elizabeth,Swarts, Jannie C.
-
p. 2862 - 2873
(2013/09/12)
-
- On the properties of the anions derived from α-deprotonation of α-(o-carboran-1-yl)- and α-ferrocenyl-1-alkylbenzotriazoles
-
The synthesis of 1-[(2-R-o-carboran-1-yl)methyl]benzotriazoles (R = Me, Ph) is described. α-Deprotonation of these compounds followed by reactions of the generated carbanions with MeI give the corresponding α-methylated products. Even at room temperature,
- Moiseev,Cherevatskaya,Verbitskaya,Glukhov,Peregudov,Kalinin
-
p. 1933 - 1942
(2013/12/04)
-
- Synthesis and structure-activity relationship studies of cytotoxic ester and ether anhydrovinblastine derivatives
-
Two new series of 3-demethoxycarbonyl-3-ester and 3-demethoxycarbonyl-3- ether methyl anhydrovinblastine derivatives were designed, synthesized, and evaluated for their inhibitory activities against human non-small-cell lung cancer (A549) and cervical epi
- Zhang, Han-Kun,Shao, Yong,Ding, Hong,Hu, Li-Hong
-
experimental part
p. 1669 - 1676
(2009/07/11)
-
- Efficient microwave access to polysubstituted amidines from imidoylbenzotriazoles
-
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.
- Katritzky, Alan R.,Cai, Chunming,Singh, Sandeep K.
-
p. 3375 - 3380
(2007/10/03)
-
- Preparation of β-keto esters and β-diketones by C-acylation/deacetylation of acetoacetic esters and acetonyl ketones with 1-acylbenzotriazoles
-
Acyl-, aroyl-, and heteroaroyl-acetic esters 6a-f and 8a-1 are prepared by reactions of 1-acylbenzotriazoles 1a-k with acetoacetic esters 5 or 7a,b in the presence of sodium hydride followed by regioselective deacetylation. Similar C-acylation/deacetylati
- Katritzky, Alan R.,Wang, Zuoquan,Wang, Mingyi,Wilkerson, Chavon R.,Hall, C. Dennis,Akhmedov, Novruz G.
-
p. 6617 - 6622
(2007/10/03)
-
- Synthesis of β-dicarbonyl compounds using 1-acylbenzotriazoles as regioselective C-acylating reagents
-
1-Acylbenzotriazoles 1 are efficient C-acylation reagents for the regioselective conversion of ketone enolates 2 into β-diketones 3.
- Katritzky, Alan R.,Pastor, Alfredo
-
p. 3679 - 3681
(2007/10/03)
-
- Polycyclic heteroaromatics from reactions of acylbenzotriazoles with aryl isocyanates
-
N-Acylbenzotriazoles react with aryl isocyanates to form, depending on the type of acyl group, compounds based on five different classes of polycyclic heteroaromatics. Higher alkanoyl-, acetyl-, acetoacetyl-, aroyl-, and cinnamoylbenzotriazoles yield, respectively, derivatives of quinoline, pyrimidino[5,4-c]quinoline, benzo[b]-1,8-naphthyridine, phenanthridine, and indolo[2,3-b]quinoline by incorporating 3, 3, 4, 2, and 2 molecules, respectively, of the isocyanate per acylbenzotriazole molecule.
- Katritzky,Huang,Voronkov,Steel
-
p. 8069 - 8073
(2007/10/03)
-
- An efficient general synthesis of 1-(benzotriazol-1-yl)alkyl esters
-
1-(Benzotriazol-1-yl)alkyl esters 2a-u were obtained in yields averaging 86% by the direct reaction of various aldehydes with the corresponding N- acylbenzotriazoles in the presence of a catalytic amount of potassium carbonate (10-25 mole %). The procedur
- Katritzky, Alan R.,Pastor, Alfredo,Voronkov, Michael V.
-
p. 777 - 781
(2007/10/03)
-
- Syntheses of β-lactones, 6: One-step synthesis of β-lactones by aldolization of ketones or aldehydes with 1-acylbenzotriazoles
-
Benzotriazolides 1 of alkanoic acids with one hydrogen atom in α-position to the carboxamide group can be deprotonated with lithium diisopropylamide or lithium hexamethyldisilazanide to amide enolates 2 which condense at -90 to -95°C with ketones or aldehydes 3 to afford benzotriazolides of O-lithiated β-hydroxylalkanoic acids 4. These reactive carboxamide derivatives cyclize with elimination of lithium benzotriazolide to the corresponding di- and trisubstituted β-lactones. With regard to the formation of β-monosubstituted β-lactones from aldehydes the use of benzotriazolides as active carboxylic acid derivatives proved to be superior to the application of the corresponding phenyl esters. An α-unsubstituted β-lactone 6 was obtained from 1-acetylbenzotriazole only with cyclohexanone. The other carbonyl compounds 3 did not provide the corresponding α-unsubstituted β-lactones 6. VCH Verlagsgesellschaft mbH, 1996.
- Wedler, Christine,Kleiner, Katharina,Kunath, Annamarie,Schick, Hans
-
p. 881 - 885
(2007/10/03)
-
- Sulfonyl derivatives of benzotriazole: Part 1. A novel approach to the activation of carboxylic acids
-
1-Acylbenzotriazoles (8, R = Me, Et, n-Bu and Ph) are prepared in good yields by fusion of benzotriazole and acid chlorides at 80 - 100°C. In cases when the corresponding acid chlorides are not available, 1-acylbenzotriazoles are conveniently available from 1-(1-methanesulfonyl) benzotriazole and the respective carboxylic acids as illustrated by the preparation of 2-, 3-, and 4-pyridoyl-, 2-pyrrolylcarbonyl- and 2-furoyl-benzotriazole in yields of 80 - 95%. Preparations of two sulfonyl derivatives of benzotriazole are also described.
- Katritzky, Alan R.,Shobana,Pernak, Juliusz,Afridi,Fan, Wei-Qiang
-
p. 7817 - 7822
(2007/10/02)
-
- A novel synthesis of esters via substitution of the benzotriazolyl group in 1-(benzotriazol-1-yl)alkyl esters with organozinc reagents
-
Aldehydes are converted by thionyl chloride and benzotriazole into 1-(1-chloroalyl)benzotriazoles which react with sodium carboxylates to give 1-(benzotriazol-1-yl)alkyl esters. 3. In the alternative route, 3 are prepared by substitution of one of the acetoxy groups in acylals with benzotriazole. The benzotriazolyl moiety in 3 is substituted by an alkyl, an aryl or an alkynyl group upon treatment with an organic reagent in a new versatile synthesis of esters 4.
- Katritzky,Rachwal,Rachwal
-
-
- Addition of Benzotriazole to Vinyl Ethers. Chemistry of the Adducts
-
Benzotriazole adds readily to ethyl vinyl ether, to 2,3-dihydrofuran, and to 3,4-dihydro-2H-pyran to form the respective α-benzotriazolyl ethers.Reactions of benzotriazole with α-methoxy derivatives of tetrahydrofuran and tetrahydropyran give similar products by substitution of benzotriazolyl for the methoxy groups.The corresponding adducts of benzotriazole and vinyl acetates are unstable and eliminate acetate anion to form geminal bis(benzotriazolyl)alkanes.The products show benzotriazol-1-yl to -2-yl isomerization. α-Benzotriazolyl derivatives of tetrahydrofuran and tetrahydropyran react with phenyl- and alkynyl-magnesium reagents to give the respective α-phenyl or α-alkynyl cycloethers.Alkylmagnesium halides by contrast attack the benzotriazolyl N-3 atom of these adducts and open the tetrahydropyranyl ring with formation of an N,N'-disubstituted o-phenylenediamine. 1H and 13C NMR spectra of the products are discussed.
- Katritzky, Alan R.,Rachwal, Stanislaw,Rachwal, Bogumila
-
p. 1717 - 1725
(2007/10/02)
-
- ETUDE DANS LA SERIE DES ORGANOSILYLAZOLES I. ACTION DES HALOGENURES D'ALKYLE, DES CHLORURES D'ACIDE ET DES CETONES HALOGENEES
-
The reactivity of organosilylamines of imidazole, pyrazole, 1,2,4-triazole and benzotriazole towards alkyl halides, acidic chlorides and halogenated ketones has been studied.Except for 1-trimethylsilylimidazole, which gives a mixed quaternary salt, reactions with primary halides lead to the corresponding 1-alkylated heterocyclic compounds in high yields; in each case only one isomer is obtained (1-alkyl-1,2,4-triazole and 1-alkylbenzotriazole).Similarly acidic chlorides give 1-acylated derivatives in quantitative yields.Finally α- or β-halogenated ketones show different behaviour and give the addition or substitution products.
- Gasparini, J. P.,Gassend, R.,Maire, J. C.,Elguero, J.
-
p. 141 - 150
(2007/10/02)
-