- 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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- 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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- 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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- ENZYME INHIBITORS
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The present subject matter relates generally to compounds having the formula (I): wherein each of X, Y, R1, R2, R3, R4, and n are as defined herein. Compounds of formula (I) may act as inhibitors of the thioredoxin reductase enzyme system. The subject matter also relates to use, formulation and preparation of the compounds. The compounds may be useful in the treatment of inflammatory and oxidative diseases and conditions. The compounds may also provide useful anti-proliferative and anti- apoptotic effects.
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Paragraph 00200
(2014/07/08)
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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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- 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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- 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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- Efficient Conversions of Carboxylic Acids into O-Alkyl, N-Alkyl and O,N-Dialkylhydroxamic Acids
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Carboxylic acids were conveniently converted into unsubstituted, N-alkyl-, O-alkyl-, and O,N-dialkylhydroxamic acids via acylbenzotriazole intermediates. The ready availability of the reagents, mild conditions, and easy handling of the intermediates are advantageous.
- Katritzky, Alan R.,Kirichenko, Nataliya,Rogovoy, Boris V.
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p. 2777 - 2780
(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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- An efficient general synthesis of 1-(benzotriazol-1-yl)alkyl esters
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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.
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p. 777 - 781
(2007/10/03)
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- Sulfonyl derivatives of benzotriazole: Part 1. A novel approach to the activation of carboxylic acids
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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
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p. 7817 - 7822
(2007/10/02)
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