- 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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- 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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- Continuous flow hydrogenation with Pd complexes of pyridine-benzotriazole ligands
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The use of continuous flow systems in chemical synthesis provides great advantages in terms of sustainability, efficiency, and safety. The ability to control reaction parameters such as temperature, pressure, and catalyst exposure in flow system enables rapid optimization of reaction conditions. In the present study, palladium complexes of 1-(piridin-2-il)-1H-benzo[d][1,2,3]triazol, N-((1H-benzo[d][1,2,3]triazol-1-il)metil)piridin-2-amin, and (1H-benzo[d][1,2,3]triazol-1-yl)(pyridin-2-yl)methanone ligands were synthesized and characterized. The catalytic activities of complexes are investigated in the hydrogenation of various alkenes such as styrene, cyclohexene, and 1-octene under continuous flow conditions. The complexes showed very high activity at 10-bar H2 pressure and 50°C for short periods of 5–10?min. The catalysts reused for 10 cycles with no significant loss of catalytic activity.
- Y?lmaz, Filiz,Hür, Deniz
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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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- 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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- 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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