112369-99-0Relevant academic research and scientific papers
Photochemical dimerization in solution of arylacrylonitrile derivatives
D'Auria, Maurizio,Racioppi, Rocco
, p. 17307 - 17316 (1997)
The photochemical irradiation of acrylonitrile derivatives bearing either aromatic or heteroaromatic rings as substituents on C-3 gives dimeric products. The reactions were carried out in acetonitrile in the presence of benzophenone as sensitizer. The mos
Associative Covalent Relay: An Oxadiazolone Strategy for Rhodium(III)-Catalyzed Synthesis of Primary Pyridinylamines
Yu, Xiaolong,Chen, Kehao,Wang, Qi,Guo, Shan,Zha, Shanke,Zhu, Jin
supporting information, p. 5222 - 5226 (2017/04/27)
A relay formalism is proposed herein for categorizing the interplay among reactants, target product, and catalytic center in transition-metal catalysis, an important factor that can dictate overall catalysis viability and efficiency. In this formalism, transition-metal catalysis can proceed by dissociative relay, associative covalent relay, and associative dative relay modes. An intriguing associative covalent relay process operates in rhodium(III)-catalyzed oxadiazolone-directed alkenyl C?H coupling with alkynes and allows efficient access to primary pyridinylamines. Although the primary pyridinylamine synthesis mechanism is posteriori rationalized, the relay formalism formulated herein can provide an important mechanistic conceptual framework for future catalyst design and reaction development.
Synthesis and anti-inflammatory activities of 4H-chromene and chromeno[2,3-b]pyridine derivatives
Chung, Shu-Ting,Huang, Wen-Hsin,Huang, Chih-Kuo,Liu, Feng-Cheng,Huang, Ren-Yeong,Wu, Chin-Chen,Lee, An-Rong
, p. 1195 - 1215 (2016/04/26)
Several derivatives of 4H-chromene and chromeno[2,3-b]pyridine were efficiently prepared under microwave irradiation in a one-pot reaction, and their anti-inflammatory activities were evaluated. Six synthetic products (1b, 1c, 1h, 2d, 2j, and 2l) exhibited more powerfully inhibited the production of tumor necrosis factor-α-induced nitric oxide (NO) than quercetin and exhibited comparable cell viability in both human and porcine chondrocytes. In particular, 2d at dosages of 10 and 20 mg/kg had a very potent anti-inflammatory effect by suppressing the formation of carrageenan-induced rat paw edema and prostaglandin E2. The results herein suggest that these compounds may have potential as structural templates in the design and development of new anti-inflammatory drugs.
Stereoselective olefination of N-sulfonyl imines with stabilized phosphonium ylides for the synthesis of electron-deficient alkenes
Fang, Fan,Li, Yuan,Tian, Shi-Kai
scheme or table, p. 1084 - 1091 (2011/04/15)
An unprecedented protocol has been developed for thestereoselective synthesis of structurally diverse electron-deficient alkenes in moderate to excellent yields from readily accessible N-sulfonyl imines and stabilized phosphonium ylides. Significantly, the olefination reaction of N-sulfonylimines with nitrile-stabilized phosphonium ylides affords an array of α,β-unsaturated nitriles with high Z selectivity, and the reactions with ester-, amide-, and ketone-stabilized phosphonium ylides afford α,β-unsaturated esters, amides, and ketones with high E selectivity, respectively. Spectroscopic analysis of the reaction mixtures and trapping of the intermediates allow plausible mechanisms to be proposed. Initialimine/ylide addition leads to the formation of betaines that cyclize to form 1,2-azaphosphetanes that subsequently eliminate iminophosphoranes to yield alkenes. For the synthesis of electron-deficient 1,2-disubstituted alkenes, the presence of an electron-withdrawing group in the betaine allows rapid interconversion between its two diastereomers through proton transfer. The Z/E selectivity for alkene synthesis is determined by the different rates at which the two betaine diastereomers form the corresponding 1,2-azaphosphetane diastereomers. In contrast, the Z/E selectivity for the synthesis of electron-deficient trisubstituted alkenes originates from the diastereoselective addition of stabilized phosphonium ylides to N-sulfonyl imines.
1-OXOTETRAHYDRO-2-BENZAZEPINES FROM 1-METHYL-3,4-DIHYDRO-5H-2-BENZAZEPINES: SYNTHESIS OF N-METHYL-7,8,9-TRIMETHOXY-2,3,4,5-TETRAHYDRO-1H-2-BENZAZEPINE
Alonso, Ricardo,Takahashi, Kimio,Schoenenberger, Bernhard,Brossi, Arnold
, p. 1595 - 1602 (2007/10/02)
A new approach to 1-oxo-2,3,4,5-tetrahydro-1H-2-benzazepines is described, the key step being the ruthenium catalyzed oxidative cleavage of 1-methylene-2-benzazepine 5 obtained by N-acetylation of the Bischler-Napieralski cyclization product of N-acetyl-3
