141694-36-2Relevant academic research and scientific papers
nBu4NI-Mediated oxidation of methyl ketones to α-ketoamides: using ammonium, primary and secondary amine-salt as an amine moiety
Wang, Dan,Zhang, Kuan,Jia, Luhan,Zhang, Danting,Zhang, Yue,Cheng, Yujia,Lin, Chang,Wang, Bo
, p. 3427 - 3434 (2017/04/24)
Presented here is the first example of synthesizing an array of primary-, secondary-, and tertiary-α-ketoamides with a non-metal catalyst nBu4NI from methyl ketones and inexpensive readily available amine/ammonium salts; the reactions proceeded smoothly under mild conditions, TBHP was used as an oxidant and the corresponding α-ketoamides were afforded in moderate to excellent yields.
Metal-free tandem oxidative aryl migration and C-C bond cleavage: Synthesis of α-ketoamides and esters from acrylic derivatives
Liu, Le,Du, Liang,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
supporting information, p. 5772 - 5775 (2015/02/19)
A novel tandem metal-free oxidative aryl migration/C-C bond-cleavage reaction, mediated by hypervalent iodine reagent, has been discovered. The presented transformation provided straightforward access to important α-ketoamide and α-ketoester derivatives from readily available acrylic derivatives via a concerted process of 1,2-aryl shift concomitant with C-C bond cleavage.
α-Keto Amides and 1,2-Diketones from N,N'-Dimethoxy-N,N'-dimethylethanediamide. A Synthetic and Mechanistic Investigation
Sibi, Mukund P.,Marvin, Mali,Sharma, Rajiv
, p. 5016 - 5023 (2007/10/03)
N,N'-Dimethoxy-N,N'-dimethylethanediamide (1), a 1,2-dicarbonyl synthon prepared from oxalyl chloride, undergoes nucleophilic displacements with Grignard reagents to provide α-keto amides 2-12 in 28-90percent yields.The synthon also undergoes double nucleophilic displacements with organolithium reagents to furnish symmetrical 1,2-diketones 15-23 in 15-84percent yields.A mechanism accounting for all the products from the reaction of 1 with nucleophiles has been proposed.Several control experiments were carried out to support the proposed mechanism.
N,N'-Dimethoxy-N,N'-dimethylethanediamide: A useful α-oxo-N-methoxy-N-methylamide and 1,2-diketone synthon
Sibi,Sharma,Paulson
, p. 1941 - 1944 (2007/10/02)
N,N'-Dimethoxy-N,N'-dimethylethanediamide on treatment with one to two equivalents of alkyl, aryl, and benzyl Grignard reagents provide α-oxo-N-methoxy-N-methylamides in good to excellent yields and on reaction with excess aryllithiums furnish moderate to good yields of symmetrical 1,2-diarylketones.
