17840-96-9Relevant 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.
TBHP/CoCl2-mediated intramolecular oxidative cyclization of N-(2-formylphenyl)amides: An approach to the construction of 4H-3,1-benzoxazin-4-ones
Yu, Junchao,Zhang-Negrerie, Daisy,Du, Yunfei
, p. 562 - 568 (2016/02/18)
The intramolecular oxidative cyclization of N-(2-formylphenyl)amides has been realized through an oxidative C(sp2)-O(sp2) bond-forming reaction between an aldehyde carbon and amide oxygen. This new strategy, which uses tert-butyl hydroperoxide (TBHP) as an oxidant and CoCl2 as the catalyst, allows for the efficient Co-catalyzed synthesis of useful benzoxazin-4-one derivatives and features readily available starting materials and mild reaction conditions. The intramolecular cyclization of N-(2-formylphenyl)amides has been realized through an oxidative C(sp2)-O(sp2) bond-forming reaction between an aldehyde carbon and amide oxygen. This new strategy, which uses tert-butyl hydroperoxide (TBHP) as the oxidant and CoCl2 as the catalyst, allows for the efficient Co-catalyzed synthesis of useful benzoxazin-4-one derivatives.
Enantioselective Synthesis of 3-Arylquinazolin-4(3H)-ones via Peptide-Catalyzed Atroposelective Bromination
Diener, Matthew E.,Metrano, Anthony J.,Kusano, Shuhei,Miller, Scott J.
supporting information, p. 12369 - 12377 (2015/10/12)
We report the development of a tertiary amine-containing β-turn peptide that catalyzes the atroposelective bromination of pharmaceutically relevant 3-arylquinazolin-4(3H)-ones (quinazolinones) with high levels of enantioinduction over a broad substrate scope. The structure of the free catalyst and the peptide-substrate complex were explored using X-ray crystallography and 2D-NOESY experiments. Quinazolinone rotational barriers about the chiral anilide axis were also studied using density functional theory calculations and are discussed in light of the high enantioselectivities observed. Mechanistic studies also suggest that the initial bromination event is stereodetermining, and the major monobromide intermediate is an atropisomerically stable, mono-ortho-substituted isomer. The observation of stereoisomerically stable monobromides stimulated the conversion of the tribromide products to other atropisomerically defined products of interest. For example, (1) a dehalogenation Suzuki-Miyaura cross-coupling sequence delivers ortho-arylated derivatives, and (2) a regioselective Buchwald-Hartwig amination procedure installs para-amine functionality. Stereochemical information was retained during these subsequent transformations.
Phosphodiesterase inhibitory properties of losartan. Design and synthesis of new lead compounds
Segarra, Victor,Crespo, M. Isabel,Pujol, Ferran,Beleta, Jorge,Domenech, Teresa,Miralpeix, Montserrat,Palacios, Jose M.,Castro, Ana,Martinez, Ana
, p. 505 - 510 (2007/10/03)
A 4-centre PDE 4 pharmacophore search has been carried out in several 3D-databases containing compounds belonging to different therapeutic areas. Losartan, an angiotensin-II antagonist, has been identified as a new lead compound for developing PDE 4 inhibitors. New families of compounds derived from losartan has been synthesized and their PDE inhibition has been measured.
