24948-82-1Relevant academic research and scientific papers
Synthesis of 4-aroyl-1,2,4-triazolidin-3-ones via ring extension in reactions of 1,2-di- and 1,2,3,3-tetraalkyldiaziridines with aroyl isocyanates
Shevtsov,Kuznetsov,Molotov,Lyssenko,Makhova
, p. 554 - 558 (2006)
Reactions of 1,2-di-and 1,2,3,3-tetraalkyldiaziridines with aroyl isocyanates involve opening of the diaziridine ring through cleavage of the C-N bond followed by cyclization of the zwitterionic intermediate into 4-aroyl-1,2,4-triazolidin-3-one derivative
N-BROMOALKYLAMINES AND NaOBr IN THE SYNTHESIS OF DIAZIRIDINES
Kuznetsov, V. V.,Makhova, N. N.,Khmel'nitskii, L. I.
, p. 1924 - 1928 (1989)
The possibility was studied of using bromine derivatives, analogous to those of chlorines, in the synthesis of 1.2-dialkyldiaziridines, and it was shown that NaOBr successfully replaces NaOCl, while RNHBr gives good results in water in the presence of an excess of amine.
Kinetic Study of the Formation of N-Chloramines
Antelo, J. M.,Arce, F.,Parajo, M.
, p. 637 - 648 (1995)
We studied the kinetics of the chlorination of amines by sodium hypochlorite in strongly alkaline aqueous solution.A reaction mechanism compatible with experimental results is proposed and discussed.
Two-step continuous flow synthesis of amide via oxidative amidation of methylarene
Fang, Zheng,Guo, Kai,He, Wei,Liu, Chengkou,Shi, Tingting,Yang, Yuhang,Yang, Zhao,Zhang, Zhimin
supporting information, (2020/02/28)
A green and efficient method for the synthesis of amides has been developed through oxidative amidation between methylarenes with amines in a two-step continuous flow system. This method integrates methylarene oxidation and amide formation into a single operation which is usually accomplished separately. Oxidation with tert-butyl hydroperoxide (TBHP) as “green” oxidant, the synthesis of amides under mild reaction conditions in continuous flow system and the utilization of methylarenes as starting material make this methodology novel and environment friendly. The practical value of this method is highlighted through the synthesis of high-profile pharmaceutical agents, acetylprocainamide.
Copper-catalyzed one-pot oxidative amidation between methylarenes and amines
Yang, Yuhang,Gu, Jiajia,Fang, Zheng,Yang, Zhao,Wei, Ping,Guo, Kai
, p. 22797 - 22801 (2017/07/10)
A new method for the direct one-pot oxidative amidation between methylarenes and amines catalyzed by copper has been developed. This method integrates methylarene oxidation and amide bond formation, which are usually accomplished separately, into a single operation. In addition, the reaction provides a relatively high yield and has a wide substrate scope. Moreover, the starting reagents are abundant and available in a convenient way at a cheaper price.
Copper-catalyzed one-pot oxidative amidation of alcohol to amide via C-H activation
Gu, Jiajia,Fang, Zheng,Yang, Yuhang,Yang, Zhao,Wan, Li,Li, Xin,Wei, Ping,Guo, Kai
, p. 89413 - 89416 (2016/10/03)
A one-pot oxidative amidation of both aliphatic and aromatic alcohols with N-chloramines, prepared in situ from many types of primary and secondary amines, was developed. This cross-coupling reaction integrates alcohol oxidation and amide bond formation, which are usually accomplished separately, into a single operation. And it was green, simple and convenient, which has a wide substrate scope and makes use of cheap, abundant, and easily available reagents. The practical value of this method is highlighted through the synthesis of a high-profile pharmaceutical agent, acetylprocainamide.
High pressure-assisted synthesis of 1,2,3-trialkyldiaziridines from N-chloroalkylamines
Kuznetsov, Vladimir V.,Syroeshkina, Julia S.,Moskvin, Dmitrii I.,Struchkova, Marina I.,Makhova, Nina N.,Zharov, Alexey A.
, p. 497 - 502 (2008/09/20)
(Chemical Equation Presented) New method for the preparation of 1,2,3-trialkyldiaziridines 1 in high yields, based on the transformation of N-chloroalkylamines 3 without using carbonyl compounds in the presence of primary aliphatic amines with the same alkyl fragment, potassium carbonate and a small amount of water in CHCl3 under high pressure (500 MPa), was developed. Diaziridines 1 can be synthesized in the same conditions using a larger amount of potassium carbonate instead of primary aliphatic amines however in lower yields. The kinetic investigations on the synthesis of 1,2-diethyl-3-methyldiaziridine 1a from N-chloroethylamine 3a have shown that the reaction leading to diaziridine 1a proceeds according to the law of the second order.
INTERACTION ENTRE LE CHLORE DE LA MONOCHLORAMINE ET L'AZOTE DES COMPOSES AMINES. FORMATION DE CHLORAMINES SUBSTITUEES
Ferriol, Michel,Gazet, Josette,Saugier-Cohen Adad, Marie-Therese
, p. 1955 - 1978 (2007/10/02)
At 25 deg C and in the pH range from 8 to 13, the kinetics and the equilibrium constant for the chlorine transfer reaction between monochloramine NH2Cl and the amines: CH3NH2, C2H5NH2, (CH3)2CHNH2, (CH3)2NH and (C2H5)2NH are investigated by spectrophotometry in aqueous medium with an ionic strength practically constant and equal to 1.03+/-0.05 M and for a concentration of total ammonia equal to 1 M.The reaction is first order with respect to each reactant and the observed rate constant, practically pH independent below 8 and above 12.8, reaches a maximum located between the pKa's of NH4+ and RR'NH2+ and depending on the nature and the concentration of the constituents used to fix pH.The reaction proceeds through two pathways involving interactions between NH2Cl and RR'NH or RR'NH2+ for which the proper rate constants are modelized according to the pKa and the substituents of each amine.
Gasphase Reactions, 60. - Methanimines RR'C=NR'': Preparation and Photoelectron Spectra
Bock, Hans,Dammel, Ralph
, p. 1961 - 1970 (2007/10/02)
Methanimines RR'C=NR'' (R, R', R'' = H, CH3) are prepared by pyrolysis of alkyl azides, or by consecutive chlorination of gaseous alkylamines at solid N-chlorosuccinimide and dehydrochlorination of the resulting N-chloroamines by passage over potassium tert-butylate in flow reactors; the reaction conditions are advantageously optimized applying PE spectroscopic realtime analysis.Their ionization patterns are assigned based on geometry-optimized MNDO calculations, radical cation state comparison, and the vibrational fine structures of individual bands.Despite their tendency to polymerize, the compounds may be condensed as monomers at low temperature and characterized by NMR.Reevaporated methanimine decomposes into H2 and HCN only above 1300 K, i.e. relative to its formation as "chemically activated" product in the methyl azide pyrolysis at a temperature higher by over 500 K.The chlorination of cyclopropylamine followed by dehydrochlorination yields a reaction mixture containing large amounts of hitherto unknown cyclopropanimine (H2C)2C=NH.
Vacuum Gas/Solid N-Chlorination: Preparative Scale Synthesis of Volatile N-Chloramines
Guillemin, J. C.,Denis, J. M.
, p. 1131 - 1133 (2007/10/02)
A simple method for the preparative scale synthesis of volatile chloramines free from impurities starting from the corresponding primary or secondary amine using N-chlorosuccinimide as chlorinating agent is described.
