73333-79-6Relevant academic research and scientific papers
Efficient synthesis of tertiary acyclic amides by the Chapman rearrangement of aryl benzimidates in ionic liquids
Epishina, Margarita A.,Kulikov, Alexander S.,Ignat'Ev, Nikolai V.,Schulte, Michael,Makhova, Nina N.
, p. 126 - 128 (2015/04/14)
The Chapman rearrangement of aryl N-arylbenzimidates to tertiary acyclic amides is accelerated in ionic liquids and proceeds at lower temperatures as 120-190°C.
Practical synthesis of aromatic dithiocarbamates
Padungros, Panuwat,Wei, Alexander
supporting information, p. 2336 - 2343 (2014/07/22)
Oxidation-sensitive N,N-diaryl dithiocarbamates (DTCs) are synthesized in good yields by the generation of metal amide salts from N-benzoyl precursors, followed by addition of CS2. para-Substituted diphenylamines are prepared by electrophilic aromatic substitution of diphenylbenzamide and saponification. Deacylation of electron-rich species such as bis(p-dimethylaminophenyl)benzamide is challenging because of the oxidative sensitivity of the anionic intermediate but could be achieved in good yield by using n-BuLi to generate a hemiaminal adduct, prior to acidification. The N,N-diaryl DTCs are stable as alkali salts and can be used to produce densely packed monolayers on gold surfaces. Copyright
A general and efficient CuBr2-catalyzed N-arylation of secondary acyclic amides
Wang, Mangang,Yu, Hua,You, Xinwen,Wu, Jun,Shang, Zhicai
, p. 2356 - 2362,7 (2020/09/16)
A general and efficient Cu(II)-catalyzed cross-coupling method is reported for the preparation of acyclic tertiary amides. Generally moderate to excellent yields and functional group tolerance were obtained with secondary acyclic amides and aryl halides as substrates in toluene. A general and efficient Cu(II)-catalyzed cross-coupling method is reported for the preparation of acyclic tertiary amides. Generally moderate to excellent yields and functional group tolerance were obtained with secondary acyclic amides and aryl halides as substrates in toluene. Copyright
A simple copper-catalyzed synthesis of tertiary acyclic amides
Racine, Emilie,Monnier, Florian,Vors, Jean-Pierre,Taillefer, Marc
supporting information; experimental part, p. 2818 - 2821 (2011/07/09)
The N-arylation of aromatic and aliphatic secondary acyclic amides, known to be poor nucleophiles, has been accomplished using a simple and cheap copper catalytic system. The corresponding tertiary acyclic amides, which can be found in numerous biologically active compounds, have been obtained in good to excellent yields.
The use of lithium amides in the palladium-mediated synthesis of [carbonyl-11C]amides
Itsenko, Oleksiy,Blom, Elisabeth,Langstroem, Bengt,Kihlberg, Tor
, p. 4337 - 4342 (2008/04/13)
Weakly nucleophilic amines were converted into the corresponding lithium amides and used in either one- or two-pot palladium-mediated reactions with [11C]carbon monoxide and aryl iodides. It was found that palladium acyl complexes may be prepared in a separate step and have sufficient life-time to be used in a subsequent reaction with a nucleophile. This two-pot procedure was used for the labelling synthesis of eleven amides (nine of which are analogues of WAY-100635, a 5-HT1A radioligand) from weakly nucleophilic amines. The results were compared to a direct one-pot procedure using lithium amides. Both approaches extend the scope of palladium-mediated carbonylation using [11C]carbon monoxide and aryl iodides allowing use of weakly nucleophilic amines. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
REARRANGEMENT OF NITRONES TO AMIDES USING CHLOROSULFONYL ISOCYANATE
Joseph, Sajan P.,Dhar, D. N.
, p. 5979 - 5983 (2007/10/02)
Reaction of chlorosulfonyl isocyanate (CSI) with nitrones 1a-n and 5a,b has been studied. α,α,N-Triaryl nitrones 1a-n react with CSI to form the N,N-diaryl arylamides 3a-n and 4i-n in good yields.In the case of α-H,α,N-diaryl nitrones 5a,b however, two compounds viz., the rearranged product 11a,b and the 1,4-dihydro tetrazines 10a,b are formed.The effect of substituents on the rearrangement has been studied.It is found that the nature of the substituents has got a profound effect on the rearrangement.We have also noted that the rearrangement is independent of the syn or anti configurations of the nitrones.
