62830-98-2Relevant academic research and scientific papers
Nuclear amination catalyzed by fungal laccases: Reaction products of p-hydroquinones and primary aromatic amines
Niedermeyer, Timo H. J.,Mikolasch, Annett,Lalk, Michael
, p. 2002 - 2008 (2005)
(Chemical Equation Presented) Nuclear amination of p-hydroquinones with primary aromatic amines was catalyzed by fungal laccases (EC 1.10.3.2) from Trametes spec. and Myceliophthora thermophila. This is the first report of laccase-catalyzed synthesis of aminoquinones. Incubation of two compounds with laccase in the presence of oxygen resulted in the formation of the corresponding monoaminated or diaminated quinones. No hydroquinonoids were formed. Observed differences in the reaction courses for different p-hydroquinones and aromatic amines with different laccases are discussed.
Synthesis and SAR of 2,3-Dihydro-1-benzofuran-4-carboxylates: Potent Salicylic Acid-Based Lead Structures against Plant Stress
Bojack, Guido,Brown, Ronald W.,Dittgen, Jan,Heinemann, Ines,Helmke, Hendrik,Hills, Martin J.,Hohmann, Sabine,Holstein, Philipp M.,Schmutzler, Dirk,Frackenpohl, Jens
, (2022/03/27)
New 2,3-dihydro-1-benzofuran-4-carboxylic acid derivatives have been identified as potent lead structures against drought and cold stress in crops starting from the synthetic exploration of stabilized analogs of the natural product lunularic acid. An optimized Lewis-acid mediated cyclization gave a short and efficient access to the envisaged 2,3-dihydro-1-benzofuran-4-carboxylates. Enantioselective approaches were investigated to assess the potential impact of the chiral center on in vivo activity. Whilst 2,3-dihydro-1-benzofuran-4-carboxamides and 2,3-dihydro-1-benzofuran-4-carboxylates carrying phenyl substituents with electron-withdrawing groups exhibited only low to moderate in vivo activity, the corresponding 2,3-dihydro-1-benzofuran-4-carboxylates carrying optimized electron-donating substituents in the phenyl moiety revealed strong in vivo activity, both against drought stress in several broad-acre crops, as well as against cold stress in corn. Remarkably, several 2,3-dihydro-1-benzofuran-4-carboxylates showed stronger efficacy than the internal standards used in our in vivo SAR study.
Peptide-Catalyzed Fragment Couplings that Form Axially Chiral Non-C2-Symmetric Biaryls
Coombs, Gavin,Sak, Marcus H.,Miller, Scott J.
supporting information, p. 2875 - 2880 (2020/01/24)
We have demonstrated that small, modular, tetrameric peptides featuring the Lewis-basic residue β-dimethylaminoalanine (Dmaa) are capable of atroposelectively coupling naphthols and ester-bearing quinones to yield non-C2-symmetric BINOL-type scaffolds with good yields and enantioselectivity. The study culminates in the asymmetric synthesis of backbone-substituted scaffolds similar to 3,3′-disubstituted BINOLs, such as (R)-TRIP, with good (94:6 e.r.) to excellent (>99.9:0.1 e.r.) enantioselectivity after recrystallization, and a diastereoselective net arylation of the minimally modified nonsteroidal anti-inflammatory drug (NSAID) naproxen.
Catalytic asymmetric synthesis of aryl diphenol the axis chiral is joint method
-
Paragraph 0049; 0050; 0051; 0052; 0053, (2017/10/31)
The invention discloses a method for catalyzing asymmetrically synthesized axially chiral biaryl diphenol. In an organic solvent, chiral phosphoric acid is taken as a catalyst, a compound shown in a formula III is obtained by reaction on a compound shown
Atroposelective Synthesis of Axially Chiral Biaryldiols via Organocatalytic Arylation of 2-Naphthols
Chen, Ye-Hui,Cheng, Dao-Juan,Zhang, Jian,Wang, Yong,Liu, Xin-Yuan,Tan, Bin
supporting information, p. 15062 - 15065 (2015/12/18)
The first phosphoric acid-catalyzed asymmetric direct arylative reactions of 2-naphthols with quinone derivatives have been developed, providing efficient access to a class of axially chiral biaryldiols in good yields with excellent enantioselectivities u
A New Selective Method for the Homolytic Alkylation and Carboxylation of Quinones by Monoesters of Oxalic Acid
Coppa, Fausta,Fontana, Francesca,Lazzarini, Edoardo,Minisci, Francesco
, p. 1299 - 1302 (2007/10/02)
Alkyl and alkoxycarbonyl radicals were generated by oxidative decarboxylation of oxalic acid monoesters by persulfate; they were then utilized for the selective substitution of quinones.
