81115-52-8Relevant academic research and scientific papers
Palladium-catalyzed C-H bond carboxylation of acetanilides: An efficient usage of N,N-dimethyloxamic acid as the carboxylate source
Wu, Yinuo,Jiang, Cheng,Wu, Deyan,Gu, Qiong,Luo, Zhang-Yi,Luo, Hai-Bin
supporting information, p. 1286 - 1289 (2016/01/15)
N,N-Dimethyloxamic acid can be successfully employed as a carboxylate precursor in the palladium-catalyzed direct C-H carboxylation of acetanilides. The reaction proceeds smoothly under mild conditions over a broad range of substrates with high functional group tolerance, affording substituted N-acyl anthranilic acids in moderate to high yields.
Synthetic applications of Pd(II)-catalyzed C-H carboxylation and mechanistic insights: Expedient routes to anthranilic acids, oxazolinones, and quinazolinones
Giri, Ramesh,Lam, Jonathan K.,Yu, Jin-Quan
supporting information; experimental part, p. 686 - 693 (2010/03/25)
A Pd(II)-catalyzed reaction protocol for the carboxylation of ortho-C-H bonds in anilides to form N-acyl anthranilic acids has been developed. This reaction procedure provides a novel and efficient strategy for the rapid assembly of biologically and pharmaceutically significant molecules, such as benzoxazinones and quinazolinones, from simple anilides without installing and removing an external directing group. The reaction conditions are also amenable to the carboxylation of N-phenyl pyrrolidinones. A monomeric palladacycle containing p-toluenesulfonate as an anionic ligand has been characterized by X-ray crystallography, and the crucial role of p-toluenesulfonic acid in the activation of C-H bonds in the presence of carbon monoxide is discussed. Identification of two key intermediates, a mixed anhydride and benzoxazinone formed by reductive elimination from organometallic Ar(CO)Pd(II)-OTs species, provides mechanistic evidence for a dual-reaction pathway.
BENZO-SEPARATED PYRAZOLOPYRIMIDINES: EXPEDITIOUS SYNTHESES OF - AND -LINKED PYRAZOLOQUINAZOLINONES
Lichtenthaler, Frieder W.,Moser, Alfred
, p. 4397 - 4400 (2007/10/02)
Syntheses for pyrazoloquinazolin-8(7H)-one (8) and its -analog 11 have been developed involving elaboration of aminoindazol-caboxylic acids 15 and 30 from correspondingly substituted methyl-nitroindazols, and subsequent anellation of the pyrimidine ring by v.Niementowski cyclization.
