26823-02-9Relevant articles and documents
Syntheses of Pyrroles, Pyridines, and Ketonitriles via Catalytic Carbopalladation of Dinitriles
Qi, Linjun,Li, Renhao,Yao, Xinrong,Zhen, Qianqian,Ye, Pengqing,Shao, Yinlin,Chen, Jiuxi
, p. 1097 - 1108 (2020/01/22)
The first example of the Pd-catalyzed addition of organoboron reagents to dinitriles, as an efficient means of preparing 2,5-diarylpyrroles and 2,6-diarylpyridines, has been discussed here. Furthermore, the highly selective carbopalladation of dinitriles with organoboron reagents to give long-chain ketonitriles has been developed as well. Based on the broad scope of substrates, excellent functional group tolerance, and use of commercially available substrates, the Pd-catalyzed addition reaction of arylboronic acid and dinitriles is expected to be significant in future synthetic procedures.
A Novel Ketonitrile Synthesis by Palladium-Catalyzed Carbonylative Coupling Reactions of Amides with Arylboronic Acids
Mai, Wen-Peng,Liu, Yang,Sui, Hong-Dai,Xiao, Yong-Mei,Mao, Pu,Lu, Kui
, p. 7814 - 7819 (2019/12/24)
A novel, efficient, and simple procedure to synthesize diverse ketonitriles by palladium-catalyzed Suzuki coupling of amides through N–C cleavage has been developed. This procedure features mild conditions, a broad substrate scope, and easily prepared substrates, providing a simple and efficient access to a variety of ketonitriles.
Nickel-Catalyzed Reductive Electrophilic Ring Opening of Cycloketone Oxime Esters with Aroyl Chlorides
Ding, Decai,Wang, Chuan
, p. 11324 - 11329 (2019/01/03)
By merging cross-electrophile coupling and C-C bond cleavage, we developed a Ni-catalyzed electrophilic ring opening of cycloketone oxime esters with aromatic acid chlorides in assistance of Mn as reductant. Notably, complete regioselectivity can be achieved in this C-C bond cleavage reaction, providing an efficient access to a variety of cyanoketones under cyanide-free conditions. A radical reaction pathway was proposed on the basis of the results of the mechanistic probing experiments.
C-C Bond-Forming Strategy by Manganese-Catalyzed Oxidative Ring-Opening Cyanation and Ethynylation of Cyclobutanol Derivatives
Ren, Rongguo,Wu, Zhen,Xu, Yan,Zhu, Chen
supporting information, p. 2866 - 2869 (2016/02/27)
A novel C-C bond-forming strategy employing manganese-catalyzed ring-opening of cyclobutanol substrates, followed by cyanation or ethynylation, is described. A cyano C1 unit and ethynyl C2 unit are regiospecifically introduced to the γ-position of ketones at room temperature, providing a mild yet powerful method for production of elusive aliphatic nitriles and alkynes. All transformations described are based on a common sequence: 1) oxidative ring-opening of cyclobutanol substrates by C-C bond cleavage; 2) radical addition to triple bonds bearing an arylsulfonyl group; and 3) radical-mediated C-S bond cleavage.
Enantioselective titanium(III)-catalyzed reductive cyclization of ketonitriles
Streuff, Jan,Feurer, Markus,Bichovski, Plamen,Frey, Georg,Gellrich, Urs
supporting information; experimental part, p. 8661 - 8664 (2012/09/21)
Reduction, please! The title reaction affords ?-hydroxyketones, a common structural motif in biologically active natural products, in good yields and high enantioselectivities at room temperature. The commercially available ansa-titanocene 1 was found to be an efficient catalyst for this process, which presumably proceeds by addition of a ketyl radical to a nitrile.
(Phenylmethoxy)phenyl Derivatives of Ω-Oxo- and Ω-Tetrazolylalkanoic Acids and Related Tetrazoles. Synthesis and Evaluation as Leukotriene D4 Receptor Antagonists
Dillard, Robert D.,Hahn, Richard A.,McCullough, Doris,Carr, F. Patrick,Rinkema, Lynn E.,et al.
, p. 2768 - 2778 (2007/10/02)
Two series of (phenylmethoxy)phenyl compounds derived from the structure of LY163443 were synthesized and evaluated as leukotriene D4 receptor antagonists.In the Ω--Ω-oxoalkanoic acid series, 5-phenyl>-3,3-dimethyl-5-oxopentanoic acid (8) was the most potent antagonist of LTD4-induced contractions of guinea pig ileum (pKB of 7.60) and LTD4 pressor response in pithed rats (ED50 of 1.4 mg/kg iv).Replacing the carboxylic acid function with 5-tetrazole gave slightly more potent compounds.Inthe Ω-alkyl>tetrazolyl>alkanoic acid series, replacing the carboxylic acid with 5-tetrazole gave compounds that were equally effective in the guinea pig ileum but more potent in vivo against the LTD4 pressor response in rat.The pKB value in the guinea pig ileum for 1--2H-tetrazol-5-yl>methyl>phenoxy>methyl>phenyl>ethanone (25) was 7.87 and the ED50 for antagonism of the LTD4 pressor response was 4.0 mg/kg iv.The sodium salts of 8 (9) and 25(26) given by the iv route of administration antagonized LTD4-induced cardiovascular alterations in anesthetized rat and LTD4-induced bronchoconstriction in guinea pig in a dose-dependent manner.Oral activity was also demonstrated against the LTD4-induced bronchoconstriction in guinea pig.
