58068-80-7Relevant articles and documents
Facile synthesis of N-acylbenzotriazoles from carboxylic acids mediated by 2,4,6-trichloro-1,3,5-triazine and triethylamine
Wet-Osot, Sirawit,Duangkamol, Chuthamat,Pattarawarapan, Mookda,Phakhodee, Wong
, p. 959 - 963 (2015/02/19)
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.
Acyloxyphosphonium versus aminophosphonium intermediates: Application to the synthesis of N-acylbenzotriazoles
Duangkam Ol, Chuthamat,Wangngae, Sirilak,Pattarawarapan, Mookda,Phakhodee, Wong
supporting information, p. 7109 - 7112 (2015/02/19)
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.
Syntheses of β-lactones, 6: One-step synthesis of β-lactones by aldolization of ketones or aldehydes with 1-acylbenzotriazoles
Wedler, Christine,Kleiner, Katharina,Kunath, Annamarie,Schick, Hans
, p. 881 - 885 (2007/10/03)
Benzotriazolides 1 of alkanoic acids with one hydrogen atom in α-position to the carboxamide group can be deprotonated with lithium diisopropylamide or lithium hexamethyldisilazanide to amide enolates 2 which condense at -90 to -95°C with ketones or aldehydes 3 to afford benzotriazolides of O-lithiated β-hydroxylalkanoic acids 4. These reactive carboxamide derivatives cyclize with elimination of lithium benzotriazolide to the corresponding di- and trisubstituted β-lactones. With regard to the formation of β-monosubstituted β-lactones from aldehydes the use of benzotriazolides as active carboxylic acid derivatives proved to be superior to the application of the corresponding phenyl esters. An α-unsubstituted β-lactone 6 was obtained from 1-acetylbenzotriazole only with cyclohexanone. The other carbonyl compounds 3 did not provide the corresponding α-unsubstituted β-lactones 6. VCH Verlagsgesellschaft mbH, 1996.
