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Cited by 58 publications
(31 citation statements)
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“…A benzotriazolyl group is easily introduced, activates molecules toward numerous transformations, and can be removed easily at the end of each reaction sequence (39-44). 1-Acylbenzotriazoles are advantageous carboxylic acid derivatives because they are stable and readily available in one step from carboxylic acids even where an acid-sensitive functionality is present (45)(46)(47). We report herein the use of this method in the synthesis of N-acylpiperidines as candidates for mosquito repellents.…”
Section: Utilization Of the Ann Model To Design And Select New Compoumentioning
confidence: 99%
“…A benzotriazolyl group is easily introduced, activates molecules toward numerous transformations, and can be removed easily at the end of each reaction sequence (39-44). 1-Acylbenzotriazoles are advantageous carboxylic acid derivatives because they are stable and readily available in one step from carboxylic acids even where an acid-sensitive functionality is present (45)(46)(47). We report herein the use of this method in the synthesis of N-acylpiperidines as candidates for mosquito repellents.…”
Section: Utilization Of the Ann Model To Design And Select New Compoumentioning
confidence: 99%
“…25 N-Acylbenzotriazoles were unaffected by heating with Grignard reagents or organozinc reagents in the presence of an equivalent of anhydrous zinc bromide (the starting materials were recovered). Neither was reaction observed in the presence of a catalytic amount of bis(triphenylphosphino)palladium(II) dichloride.…”
Section: Resultsmentioning
confidence: 99%
“…23 N-Acylbenzotriazoles are advantageous carboxylic acid derivatives in that they are stable and easily prepared in one step from the carboxylic acids even in cases where an acid-sensitive functionality is present. 25 Their reactivity is significantly enhanced by Lewis acids (especially, Zn 2+ salts), and that makes them convertible by less active organometallic reagents. Viewing these compounds as potentially useful intermediates for transformations of carboxylic acids into ketones, we attempted the reaction of readily available N-acylbenzotriazoles with a number of organozinc reagents in the presence of a Lewis acid and a Pd 2+ or Ni catalyst.…”
Section: Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…N-acylbenzotriazoles provide excellent alternatives to Friedel Crafts and Vilsmeier Haack acylations methodologies and can be easily used when the corresponding acid chlorides are not readily available. Previously N-acylbenzotriazoles were prepared by two methods: (i) by heating acid chloride and benzotriazole directly without the use of any solvent (ii) carboxylic acid in tetrahydrofuran with 1-(methylsulfonyl)-1H-1,2,3 benzotriazoles in the presence of triethylamine ( ) 3) . Besides this other tedious methods for synthesis of N-acylbenzotriazoles were also known [4][5][6] .…”
Section: Introductionmentioning
confidence: 99%