- One-pot synthesis of N-imidoylbenzotriazoles via benzotriazole-mediated Beckmann rearrangement of oximes
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(Matrix presented) N-Imidoylbenzotriazoles 5a-I are obtained under mild conditions in variable yields (20-87%) by reactions of oximes 2a-I with BtTs 1 via a Beckmann rearrangement.
- Katritzky, Alan R.,Monteux, Daphne A.,Tymoshenko, Dmytro O.
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- Convenient sulfonylation of benzotriazoles with the in situ–generated sulfonyl bromides
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A convenient procedure is developed for the preparation of N-sulfonylbenzotriazoles from sodium sulfinates, benzotriazoles, and sodium bromide in the present of m-chloroperbenzoic acid as oxidant. This radical sulfonylation proceeds efficiently at room te
- Wu, Sixue,Zhang, Yikun,Yan, Jie
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- Synthesis of sulfonyl azides
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1-(Alkylsulfonyl)- and 1-(arylsulfonyl)benzotriazoles react with sodium azide in acetonitrile to give the corresponding alkanesulfonyl and arenesulfonyl azides. Georg Thieme Verlag Stuttgart.
- Katritzky, Alan,Widyan, Khalid,Gyanda, Kapil
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- Sodium hydrogen exchanger inhibitory activity of benzotriazole derivatives
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Series of benzotriazole derivatives were synthesized and evaluated for their Sodium hydrogen exchanger-1 inhibitory potential. All compounds inhibit Sodium hydrogen exchanger-1 in the in-vitro platelet swelling assay. This is perhaps the first report of NHE-1 inhibitory activity of benzotriazole. The 1-alkyl benzotriazole derivatives were found to be more active than the 2-alkyl isomers. The activity increases with increase in chain length of alkyl moiety. Potency increased from that of benzotriazole (IC50= 192.68 μM) to heptyl derivative (compound 13; IC50= 59.23 μM). Introduction of electronegative oxygen atom further increased potency as shown by the benzoyl (compound 16, IC50= 51.57 μM) and sulfonyl groups (compound 17, IC50= 50.89 μM; compound 18, IC50= 49.95 μM).
- Singh, Dhandeep,Silakari, Om
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- Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides
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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
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supporting information
p. 58 - 63
(2021/12/27)
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- Transition-Metal-Free and Visible-Light-Mediated Desulfonylation and Dehalogenation Reactions: Hantzsch Ester Anion as Electron and Hydrogen Atom Donor
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Novel approaches for N- and O-desulfonylation under room temperature (rt) and transition-metal-free conditions have been developed. The first methodology involves the transformation of a variety of N-sulfonyl heterocycles and phenyl benzenesulfonates to the corresponding desulfonylated products in good to excellent yields using only KOtBu in dimethyl sulfoxide (DMSO) at rt. Alternately, a visible light method has been used for deprotection of N-methyl-N-arylsulfonamides with Hantzsch ester (HE) anion serving as the visible-light-absorbing reagent and electron and hydrogen atom donor to promote the desulfonylation reaction. The HE anion can be easily prepared in situ by reaction of the corresponding HE with KOtBu in DMSO at rt. Both protocols were further explored in terms of synthetic scope as well as mechanistic aspects to rationalize key features of desulfonylation processes. Furthermore, the HE anion induces reductive dehalogenation reaction of aryl halides under visible light irradiation.
- Heredia, Micaela D.,Guerra, Walter D.,Barolo, Silvia M.,Fornasier, Santiago J.,Rossi, Roberto A.,Budén, Mariá E.
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supporting information
p. 13481 - 13494
(2020/12/15)
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- Synthesis of Structurally Diverse Benzotriazoles via Rapid Diazotization and Intramolecular Cyclization of 1,2-Aryldiamines
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An operationally simple method has been developed for the preparation of N-unsubstituted benzotriazoles by diazotization and intramolecular cyclization of a wide range of 1,2-aryldiamines under mild conditions, using a polymer-supported nitrite reagent and p-tosic acid. The functional group tolerance of this approach was further demonstrated with effective activation and cyclization of N-alkyl, -aryl, and -acyl ortho-aminoanilines leading to the synthesis of N1-substituted benzotriazoles. The synthetic utility of this one-pot heterocyclization process was exemplified with the preparation of a number of biologically and medicinally important benzotriazole scaffolds, including an α-amino acid analogue.
- Faggyas, Réka J.,Sloan, Nikki L.,Buijs, Ned,Sutherland, Andrew
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p. 5344 - 5353
(2019/05/21)
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- Tert -Butyl nitrite mediated nitrogen transfer reactions: Synthesis of benzotriazoles and azides at room temperature
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A conversion of o-phenylenediamines into benzotriazoles was achieved at room temperature using tert-butyl nitrite. The optimized conditions are also well suited for the transformation of sulfonyl and acyl hydrazines into corresponding azides. This protocol does not require any catalyst or acidic medium. The desired products were obtained in excellent yields in a short span of time.
- Azeez, Sadaf,Chaudhary, Priyanka,Sureshbabu, Popuri,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
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supporting information
p. 6902 - 6907
(2018/10/02)
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- Synthesis of sulfonamides from azoles and sodium sulfinates at ambient temperature
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NBS or NIS mediated direct S[sbnd]N bond formation between azoles and sodium sulfinates is described. The reaction shows good substrate scope and tolerates a wide range of functionalities in both azoles and sodium sulfinate substrates. Pyrazoles are also suitable for this method, various 4-halopyrazoles derivatives were obtained by using N-halosuccinimide (NXS) as the halogen source.
- Fu, Lili,Bao, Xiaodong,Li, Shanshan,Wang, Lingtian,Liu, Zhiguo,Chen, Wanzhi,Xia, Qinqin,Liang, Guang
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p. 2504 - 2511
(2017/04/03)
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- Base free regioselective synthesis of α-triazolylazine derivatives
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A regioselective α-heteroarylation followed by deoxygenation towards the synthesis of variety of azine triazole from simple azine N-oxides derivatives and N-tosyl-1,2,3-triazoles has been described. The reaction is metal free and base free with shorter reaction time, high yields and a broad substrate scope.
- Harisha, Mysore Bhyrappa,Nagaraj, Muthupandi,Muthusubramanian, Shanmugam,Bhuvanesh, Nattamai
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p. 58118 - 58124
(2016/07/06)
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- Iodine-catalyzed N-sulfonylation of benzotriazoles with sodium sulfinates under mild conditions
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A new and convenient procedure is developed for the preparation of N-sulfonylbenzotriazoles from sodium sulfinates and benzotriazoles using molecular iodine as catalyst via the S[sbnd]N bond formation reaction. This catalytic radical sulfonylation proceed
- Wu, Si-Xue,Zhang, Yi-Kun,Shi, Hong-Wei,Yan, Jie
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p. 1519 - 1522
(2016/09/23)
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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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- Enantioselective organocatalytic approach to the synthesis of α,α-disubstituted cyanosulfones
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(Chemical Equation Presented) Optically pure cyano tert-alkyl sulfones have been obtained by organocatalytic enantioselective Michael addition of α-substituted cyanosulfones to vinyl ketones using cinchona alkaloids as catalysts. The best results were obt
- Cid, M. Belén,López-Cantarero, Jesús,Duce, Sara,Ruano, José Luis García
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supporting information; experimental part
p. 431 - 434
(2009/04/10)
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- A General and Efficient Synthesis of Sulfonylbenzotriazoles from N-Chlorobenzotriazole and Sulfinic Acid Salts
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One-pot reactions of sulfinic acid salts (produced from organometallic reagents with SO2) with N-chlorobenzotriazole gave the corresponding N-alkane-, N-arene-, and N-heteroenesulfonylbenzotriazoles 3a-j in 41-93% yields. Reagents 3a-j are effi
- Katritzky, Alan R.,Rodriguez-Garcia, Valerie,Nair, Satheesh K.
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p. 1849 - 1852
(2007/10/03)
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- α-benzotriazolylpyridines and their N-oxides
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α-Benzotriazolyl-substituted pyridines, -quinolines and -isoquinolines have been prepared by reactions of pyridine, quinoline and isoquinoline N-oxides with 1-tosylbenzotriazole in the presence of triethylamine. Treatment of α-benzotriazolylpyridines, -quinolines and -isoquinolines with hydrogen peroxide in glacial acetic acid afforded N-oxides, the structures of which were determined by X-Ray crystallography. Reactions of 1-(2-pyridinyl)-benzotriazole with alkyl halides or tosylates led to the corresponding N-alkylpyridinium salts.
- Katritzky, Alan R.,Kurz, Thomas,Zhang, Suoming,Voronkov, Michael,Steel, Peter J.
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p. 1703 - 1710
(2007/10/03)
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- Preparation, Characterization and Reactions of Novel Vicinal Dibenzotriazol-1-yl Derivatives of Benzotriazole and Glyoxal
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A variety of novel 1,2-disubstituted-1,2-di(benzotriazol-1-yl)ethane and 1,2-di(benzotriazol-1-yl)ethylene derivatives were prepared from the adduct of benzotriazole and glyoxal.
- Katritzky, Alan R.,Fan, Wei-Quiang
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p. 1543 - 1547
(2007/10/02)
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