- Trichloroisocyanuric Acid Mediated High-Yielding Synthesis of N -Acylbenzotriazoles under Mild Reaction Conditions
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N -Acylbenzotriazoles are achieved in good yields from the corresponding carboxylic acids by using only 0.35 equivalent of trichloroisocyanuric acid and 1.2 equivalents of PPh 3. The salient features of the developed reaction path include an ec
- Singh, Mala,Singh, Anoop S.,Mishra, Nidhi,Agrahari, Anand K.,Tiwari, Vinod K.
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p. 2183 - 2190
(2019/05/10)
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- An Improved N-Acylation of 1 H-Benzotriazole Using 2,2′-Dipyridyl?-di?-sulfide and Triphenylphosphine
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A novel path has been developed for the conversion of carboxylic acids into the corresponding N-acylbenzotriazoles by using 2,2′-dipyridyl disulfide/PPh 3 in anhydrous dichloromethane in the presence of 1 H-benzotriazole. Mild reaction conditio
- Singh, Anoop S.,Agrahari, Anand K.,Mishra, Nidhi,Singh, Mala,Tiwari, Vinod K.
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p. 470 - 476
(2019/01/10)
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- Visible-Light-Induced C(sp2)-P Bond Formation by Denitrogenative Coupling of Benzotriazoles with Phosphites
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A visible-light-induced denitrogenative phosphorylation of benzotriazoles is presented, in which diverse substituted aryl phosphonates could be obtained in good to excellent yields. This efficient protocol exhibits good tolerance with various functional g
- Jian, Yong,Chen, Ming,Huang, Binbin,Jia, Wei,Yang, Chao,Xia, Wujiong
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supporting information
p. 5370 - 5374
(2018/09/13)
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- A new methodology for the synthesis of N-acylbenzotriazoles
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A facile and economic path for an easy access of diverse N-acylbenzotriazoles from carboxylic acid has been devised using NBS/PPh3 in anhydrous dichloromethane. High yield of product was obtained at room temperature in one hour reaction time under mild reaction conditions.
- Singh, Anoop S.,Agrahari, Anand K.,Singh, Mala,Mishra, Nidhi,Tiwari, Vinod K.
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- Accessing N-Acyl Azoles via Oxoammonium Salt-Mediated Oxidative Amidation
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An operationally simple, robust, metal-free approach to the synthesis of N-acyl azoles from both alcohols and aldehydes is described. Oxidative amidation is facilitated by a commercially available organic oxidant (4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) and proceeds under very mild conditions for an array of structurally diverse substrates. Tandem reactions of these activated amides, such as transamidation and esterification, enable further elaboration. Also, the spent oxidant can be recovered and used to regenerate the oxoammonium salt.
- Ovian, John M.,Kelly, Christopher B.,Pistritto, Vincent A.,Leadbeater, Nicholas E.
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supporting information
p. 1286 - 1289
(2017/03/22)
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- Oxidative functionalisation of alcohols and aldehydes via the merger of oxoammonium cations and photoredox catalysis
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We present a new paradigm for nitroxyl-mediated processes via the merger of oxoammonium cation-mediated oxidation with visible-light photoredox catalysis. The integration of these two forms of catalysis has been realised for the oxidative amidation of aldehydes, furnishing N-acylated heterocycles. Extension of this process to the oxidative amidation of alcohols via the intermediacy of an aldehyde was successfully pursued, thus proffering a general oxidation platform. The activated amides synthesised here are excellent synthetic handles for acylation.
- Nandi, Jyoti,Ovian, John M,Kelly, Christopher B,Leadbeater, Nicholas E.
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supporting information
p. 8295 - 8301
(2017/10/19)
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- An efficient one-pot synthesis of: N, N ′-disubstituted ureas and carbamates from N -acylbenzotriazoles
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A facile and high-yielding one-pot synthesis of carbamates and N,N′-disubstituted symmetrical ureas from N-acylbenzotriazoles has been devised. It is believed that, the intermediate acyl-azide undergo Curtius rearrangement and in different solvents gives different products i.e. carbamates in alcohols and N,N′-disubstituted symmetrical urea in THF.
- Singh, Anoop S.,Kumar, Dhananjay,Mishra, Nidhi,Tiwari, Vinod K.
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p. 84512 - 84522
(2016/10/12)
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- Identification of a novel class of quinoline-oxadiazole hybrids as anti-tuberculosis agents
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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
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p. 645 - 649
(2016/01/09)
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- TCT-mediated synthesis of N-acylbenzotriazoles in aqueous media
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The synthesis of N-acylbenzotriazoles has been demonstrated by the 2,4,6-trichloro-1,3,5-triazine (TCT)-mediated condensation of carboxylic acids with 1H-benzotriazole in aqueous media. In saturated aqueous sodium bicarbonate, TCT was found to be relatively stable and functioned as an efficient acid activator in the acyl transfer process. This operationally simple and economic method allows the scalable synthesis of N-acylbenzotriazoles in good to excellent yields.
- Wet-Osot, Sirawit,Phakhodee, Wong,Pattarawarapan, Mookda
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p. 6998 - 7000
(2015/11/27)
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- Facile synthesis of N-acylbenzotriazoles from carboxylic acids mediated by 2,4,6-trichloro-1,3,5-triazine and triethylamine
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Abstract A facile, efficient, and economic method toward N-acylbenzotriazoles was reported using 2,4,6-trichloro-1,3,5-triazine in combination with triethylamine as a carboxylic acid activator. Through reacting 1H-benzotriazole with the generated triacylated triazine intermediate, a series of N-acylbenzotriazoles could be rapidly prepared in high yields without column chromatography.
- Wet-Osot, Sirawit,Duangkamol, Chuthamat,Pattarawarapan, Mookda,Phakhodee, Wong
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p. 959 - 963
(2015/02/19)
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- Acyloxyphosphonium versus aminophosphonium intermediates: Application to the synthesis of N-acylbenzotriazoles
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In attempts to convert carboxylic acids directly into N-acylbenzotriazoles by using Ph3P/I2 as an acid-activating system, the outcome of the reaction is reversed from no reaction to almost quantitative yield of the expected product simply by switching the order of the addition of the reagents to the presumed acyloxyphosphonium intermediate. If triethylamine was present before treatment with 1H-benzotriazole, anhydride was always exclusively generated without a detectable amount of the expected product. However, if the base was applied after the addition of 1H-benzotriazole, the reaction proceeded smoothly to afford N-acylbenzotriazoles in good to excellent yields within short reaction times. 31P NMR spectroscopy revealed the presence of a benzotriazophosphonium species in preventing the formation of the anhydride by attack of the carboxylate anion at the acyl function of the acyloxyphosphonium salt.
- Duangkam Ol, Chuthamat,Wangngae, Sirilak,Pattarawarapan, Mookda,Phakhodee, Wong
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supporting information
p. 7109 - 7112
(2015/02/19)
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- Macrocyclic peptoids by selective s-acylation of cysteine esters
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Optimized selective S-acylations of cysteine esters gave intermediates for the synthesis of macrocyclic peptoids by a benzotriazole-based method. Georg Thieme Verlag Stuttgart · New York.
- Ibrahim, Mohamed A.,Panda, Siva S.,Nhon, Linda,Hamed, Ahmed,El-Feky, Said A.,Katritzky, Alan R.
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p. 767 - 772
(2013/04/10)
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- Selective synthesis and structural elucidation of S-acyl- and N-acylcysteines
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(Chemical Equation Presented) N-(Acyl)-1H-benzotriazoles 6a-f react with L-cysteine 5 at 20°C to give exclusively (i) N-acyl-L-cysteines 8a-e in the presence of triethylamine in CH3CN-H2O (3:1), but (ii) S-acyl-L-cysteines 7a-e in CH
- Katritzky, Alan R.,Tala, Srinivasa R.,Abo-Dya, Nader E.,Gyanda, Kapil,El-Gendy, Bahaa El-Dien M.,Abdel-Samii, Zakaria K.,Steel, Peter J.
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body text
p. 7165 - 7167
(2009/12/09)
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- Preparation of polyfunctional acyl azides
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(Chemical Equation Presented) A general synthesis of acyl azides from the corresponding N-acyl benzotriazoles is described. The procedure affords acyl azides in good yields and avoids the use of acid activators and NO+ equivalents typically emp
- Katritzky, Alan R.,Widyan, Khalid,Kirichenko, Kostyantyn
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p. 5802 - 5804
(2008/02/09)
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- Efficient microwave access to polysubstituted amidines from imidoylbenzotriazoles
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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.
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p. 3375 - 3380
(2007/10/03)
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- Gas-phase thermolysis of benzotriazole derivatives. Part 3: Kinetic and mechanistic evidence for biradical intermediates in pyrolysis of aroylbenzotriazoles and related compounds
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Gas-phase pyrolysis (static and FVP) of 1-aroylbenzotriazoles gave the corresponding substituted benzoxazole, benzimidazole, benzamide, N-phenylbenzamide, phenanthridin-6(5H)-one derivatives and 1- cyanocyclopentadiene. The present kinetic and mechanistic findings also provide further evidence of the involvement of biradical or carbene reactive intermediates in the reaction pathway of gas-phase pyrolysis of benzotriazoles.
- Al-Awadi, Nouria A.,George, Bobby J.,Dib, Hicham H.,Ibrahim, Maher R.,Ibrahim, Yehia A.,El-Dusouqui, Osman M. E.
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p. 8257 - 8263
(2007/10/03)
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- Facile Syntheses of Oxazolines and Thiazolines with N-Acylbenzotriazoles under Microwave Irradiation
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Microwave reactions of 2-amino-2-methyl-1-propanol (2) or 2-aminoethanethiol hydrochloride (4) with readily available N-acylbenzotriazoles 1a-j in the presence of SOCl2 produced 2-substituted 2-oxazolines 3a-j in 84-98% yields and 2-substituted
- Katritzky, Alan R.,Cai, Chunming,Suzuki, Kazuyuki,Singh, Sandeep K.
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p. 811 - 814
(2007/10/03)
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- C-acylation of 2-methylfuran and thiophene using N-acylbenzotriazoles
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Reactions of 2-methylfuran and thiophene with readily available N-acylbenzotriazoles (RCOBt, where R = 4-tolyl, 4-methoxyphenyl, benzyl, 4-nitrophenyl, 4-diethylaminophenyl, 2-pyridyl and 1-naphthyl) in the presence of TiCl4 or ZnBr2 produced 2-methyl-4-acylfurans 2a-e and 2-acylthiophenes 3a-f in average yields of 54 % and 75 %, respectively. Literature yields for the preparation of the same compounds are significantly lower.
- Katritzky, Alan R.,Suzuki, Kazuyuki,Singh, Sandeep K.
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p. 175 - 178
(2007/10/03)
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- Regiospecific C-acylation of pyrroles and indoles using N-acylbenzotriazoles
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Reactions of pyrrole (2) or 1-methylpyrrole (4) with readily available N-acylbenzotriazoles 1a - g (RCOBt, where R = 4-tolyl, 4-nitrophenyl, 4-diethylaminophenyl, 2-furyl, 2-pyridyl, 2-indolyl, or 2-pyrrolyl) in the presence of TiCl4 produced 2
- Katritzky, Alan R.,Suzuki, Kazuyuki,Singh, Sandeep K.,He, Hai-Ying
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p. 5720 - 5723
(2007/10/03)
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- Solid-phase preparation of amides using N-acylbenzotriazoles
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Wang resin linked amines were efficiently converted into amides using acylbenzotriazoles. Cleavage of resins gave the desired amides 7Aa-Gf in 30-99% yields with good to excellent purities.
- Katritzky, Alan R,Rogovoy, Boris V,Kirichenko, Nataliya,Vvedensky, Vladimir
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p. 1809 - 1811
(2007/10/03)
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- Hypervalent iodine in synthesis. 65: A new route to synthesize N-acylbenzotriazoles via palladium catalyzed carbonylation of benzotriazole and hypervalent iodonium salts in the presence of carbon monoxide
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N-acylbenzotriazoles are obtained directly in fair yields by palladium-catalyzed carbonylation of diaryliodonium salts with benzotriazoles in the presence of carbon monoxide.
- Wang,Chen
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p. 1633 - 1637
(2007/10/03)
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- N-acylbenzotriazoles: Neutral acylating reagents for the preparation of primary, secondary, and tertiary amides
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Readily available N-acylbenzotriazoles 2a-q efficiently acylate aqueous ammonia and primary and secondary amines to give primary, secondary, and tertiary amides in good to excellent yields. The wide applicability of the procedure is illustrated by the preparation of (i) α-hydroxyamides from α-hydroxy acids and of (ii) perfluoroalkylated amides.
- Katritzky,He,Suzuki
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p. 8210 - 8213
(2007/10/03)
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