1738-54-1Relevant academic research and scientific papers
Synthesis of diacylamines and the preparation of α-amino-acylureas, a new type of α-amino acid derivatives
Weisz, Imre,Roboz, John,Wolf, Imre,Szabo, Jozsef,Bekesi, J. George
, p. 3241 - 3244 (1998)
Sixteen new and one known unsymmetrical open-chain diacylamines were synthesized by sodium methoxide catalyzed acylation of amides with carboxylic esters and acylamino-carboxylic esters, or acylureas with acylamino- carboxylic esters and α-amino acid esters.
The Nature of the Transition State in Amides Pyrolysis. The Rates of Pyrolysis of N-benzoyl and N-acetylpropanamide, N-benzoyl and N-acetyl-2-methylpropanamide, and N-thioacetylpropanamide
Al-Awadi, Nouria A.,Al-Omran, Fatima A.,Mathew, Tommy
, p. 1 - 6 (1995)
The rates of gas-phase elimination reactions of N-benzoyl and N-acetyl-propanamide and N-benzoyl and N-acetyl-2-methylpropanamide are measured and discussed.They undergo unimolecular first-order elimination reactions.The reactivities of N-benzoylamides have been compared with each other and with those of N-acetylamides.The kinetic data together with the product analysis reveals that, the statistical factor of the availability of β-hydrogen atoms for elimination as well as steric factor are obscured by polar factor in gas-phase elimination reactions of N-benzoylamides while the statistical factor rather than electronic effect operates in each of N-acetylamides.
Visible-Light-Driven Oxidation of N -Alkylamides to Imides Using Oxone/H 2 O and Catalytic KBr
Mei, Chong,Hu, Yixin,Lu, Wenjun
, p. 2999 - 3005 (2018/05/25)
Imides are prepared conveniently by visible-light-driven oxidations of various N -alkylamides under mild conditions. The majority of the reactions proceed efficiently by using Oxone as the oxidant in the presence of a catalytic amount of KBr in H 2 O/CH 2 Cl 2 under irradiation by an 8 W white LED at room temperature. Experimental studies suggest that an imine, obtained from the substrate amide via a radical process, is the key intermediate.
TBHP/TEMPO-mediated oxidative synthesis of imides from amides
Yu, Hui,Chen, Yuegang,Zhang, Yonghao
, p. 531 - 534 (2015/05/27)
A new protocol for the synthesis of imides has been developed. In the presence of copper catalyst, N-benzylamides were oxidized to the corresponding imides by TBHP/TEMPO system in moderate to good yields. Imides were synthesized through the oxidation of N-benzylamides by TBHP/TEMPO system in moderate to good yields.
Synthesis of 1,3,5-trisubstituted-1,2,4-triazoles by microwave-assisted N-acylation of amide derivatives and the consecutive reaction with hydrazine hydrochlorides
Lee, Jongbok,Hong, Myengchan,Jung, Yoonchul,Cho, Eun Jin,Rhee, Hakjune
experimental part, p. 2045 - 2051 (2012/04/10)
Facile and efficient procedures for the N-acylation reaction of amide derivatives with various acid anhydrides and the cyclization reaction of N-acylated amide derivatives with various hydrazine hydrochlorides were described. The reactions were carried out under microwave irradiation to give products in good yields in a few minutes. The synthesis of 1,3,5-trisubstituted- 1,2,4-triazoles from benzamides can also be accomplished in a simple one-pot sequential reaction.
Ceric ammonium nitrate promoted oxidation of oxazoles
Evans, David A.,Nagorny, Pavel,Xu, Risheng
, p. 5669 - 5671 (2007/10/03)
The ceric ammonium nitrate promoted oxidations of 4,5-diphenyloxazoles and oxazoles with various substitution patterns have been investigated. This transformation results in the formation of the corresponding imide in good yield and tolerates a wide variety of functional groups and substituents on the oxazole moiety.
Novel chromium(VI) catalyzed oxidation of N-alkylamides to imides with periodic acid
Xu, Liang,Zhang, Suhong,Trudell, Mark L.
, p. 1668 - 1669 (2007/10/03)
A novel and practical procedure for preparation of imides is described using chromium(VI) oxide to catalyze the oxidation of N-alkylamides with periodic acid in the presence of acetic anhydride in acetonitrile.
An Unexpected Ring Enlargemant of 3-(Dimethylamino)-2,2-dimethyl-2H-azirine to 4,5-Dihydropyridin-2(3H)-one Derivatives
Hugener, Martin,Heimgartner, Heinz
, p. 1863 - 1878 (2007/10/02)
The reaction of 3-(dimethylamino)-2,2-dimethyl-2H-azirine (1a) and 4,4-disubstituted 2-(trifluoromethyl)-1,3-oxazol-5(4H)-ones 7 in MeCN at 70 deg afforded 5-(dimethylamino)-3,6-dihydropyrazin-2(1H)-ones 10 (Scheme 4), whereas no reaction could be observed between 1a and 2-allyl-4-phenyl-2-(trifluoromethyl)-1,3-oxazol-5(2H)-one (8a) or 4,4-dibenzyl-2-phenyl-1,3-oxazol-5(4H)-one (9).The formation of 10 is rationalized by a mechanism via nucleophilic attack of 1a onto 7.The failure of a reaction with 9 shows that only activated 1,3-oxazol-5(4H)-ones bearing electron-withdrawing substituents do react as electrophiles with 1a.The amino-azirine 1a and 2,4-disubstituted 1,3-oxazol-5(4H)-ones 2b-e in refluxing MeCN undergo a novel ring enlargement to 4,5-dihydropyridin-2(3H)-ones 11 (Scheme 5).Several side products were observed in these reactions.Two different reaction mechanisms for the formation of 11 are proposed: either 1a undergoes a nucleophilic addition onto the open-chain ketene tautomer of 2 (Scheme 6), or 2 reacts as CH-acidic compound (Scheme 7).
AN EFFICIENT TRANSFORMATION OF N-ACYL-α-AMINO ACIDS INTO DIACYLAMINES VIA 2,4-DISUBSTITUTED OXAZOL-5(4H)-ONES
Suda, Kohji,Hino, Fumio,Yijima, Chino
, p. 882 - 885 (2007/10/02)
Base-catalyzed oxygenative decarboxylation of a variety of 2,4-disubstituted oxazol-5(4H)-ones in benzene with triethylamine or in dimethylsulfoxide with potassium tert-butoxide gives diacylamines.KEYWORDS - base-catalyzed autooxidation; selective oxygenation; decarboxylation; oxazol-5(4H)-one; N-acyl-α-amino acid; diacylamine
