46721-85-1Relevant academic research and scientific papers
Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones
Dong, Guangbin,Xu, Yan,Zhou, Xukai
supporting information, p. 20042 - 20048 (2021/12/03)
The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.
From Phenylhydrazone to 1H-1,2,4-Triazoles via Nitrification, Reduction and Cyclization
Hao, Liqiang,Wang, Guodong,Sun, Jian,Xu, Jun,Li, Hongshuang,Duan, Guiyun,Xia, Chengcai,Zhang, Pengfei
supporting information, p. 1657 - 1662 (2020/03/19)
Herein we report an annulation of phenylhydrazone via a tandem nitrification, reduction, cyclization protocol employing cobalt nitrate and 1,2-dichloroethane to produce substituted 1H-1,2,4-triazoles. Notably, 1,2-dichloroethane serves both the solvent and a hydrogen source for transfer hydrogenation. This methodology works under mild conditions, providing a direct approach for the synthesis of 1H-1,2,4-triazoles. (Figure presented.).
A Study of Boratriazaroles: An Underdeveloped Class of Heterocycles
Liew, Sean K.,Holownia, Aleksandra,Tilley, Andrew J.,Carrera, Elisa I.,Seferos, Dwight S.,Yudin, Andrei K.
, p. 10444 - 10453 (2016/11/17)
Boratriazaroles were discovered in the late 1960s, and since then, a variety of substituted boratriazarole derivatives have been prepared. However, no study has compared the properties of these BN heterocycles with their carbon-based analogues. In this work, we have prepared a series of boratriazarole derivatives and have investigated how structural variations in the five-member heterocycle affect photophysical and electronic properties. Boratriazaroles exhibit absorption and emission spectra comparable to those of their azacycle analogues but have a markedly lower quantum yield. The quantum yield can be increased with the incorporation of a 2-pyridyl substitution on the boratriazaroles, and the structural and optoelectronic properties are further influenced by the nature of the B-aryl substituent. Introducing an electron-deficient p-cyano group on the B-phenyl substituent creates a twisted intramolecular charge transfer state that causes a large Stokes shift and positive solvatochromism. Our work should serve to guide future synthetic efforts toward the application of boratriazaroles in materials science.
Investigating Scale-Up and Further Applications of DABAL-Me3 Promoted Amide Synthesis
Lee, Darren S.,Amara, Zacharias,Poliakoff, Martyn,Harman, Thomas,Reid, Gary,Rhodes, Barrie,Brough, Steve,McInally, Thomas,Woodward, Simon
, p. 831 - 840 (2015/07/27)
Methods for the batch scale up of DABAL-Me3 promoted direct ester to amide synthesis have been demonstrated at 10-100 g scales using a tert-amide model compound. Procedures for 20 g scale couplings in standard laboratory glassware and up to 0.1 kg in industry-standard jacketed glass reactors in near quantitative yields are given. A derivative of the anticancer agent Imatinib (Gleevec) has been synthesized on a 26 g scale (98% yield, >98% purity) establishing DABAL-Me3 as a potential alternative for the synthesis of amides in API scale preparations. Continuous flow methodology provides a method for larger scales (productivities of >50 g h-1). In addition, nitriles were coupled to primary amines and hydrazines with DABAL-Me3, resulting in the clean formation of free amidines (16 examples) and amidrazones.
Inhibiteurs mixtes des voies de la cyclooxygenase et des lipoxygenases: synthese et activite de derives hydrazoniques
Ghiglieri-Bertez, Chantal,Coquelet, Claude,Alazet, Alain,Bonne, Claude
, p. 147 - 152 (2007/10/02)
Dual inhibitors of the cyclooxygenase and lipoxygenase pathways: synthesis and activity of hydrazone derivatives.Non-steroidal anti-inflammatory drugs (NSAIDs) act by preventing prostaglandin production.In recent years, research on non-steroid dual inhibitors of prostaglandin and leukotriene biosyntheses has been developed.These compounds should represent a new class of anti-inflammatory drugs, with a wider spectrum of activity than classical NSAIDs.The present paper reports the synthesis of hydrazone derivatives.The effect of various substitutions is studied on platelet cyclooxygenase (i.e. prostaglandin synthesis) and on leukocyte 5-lipoxygenase (i.e. leukotriene synthesis).Among the 50 tested compounds, 2 hydrazone derivatives were selected for their significant dual inhibitory potency: 2-acetylthiophene-2-thiazolylhydrazone 5g, and N-phenyl benzimidrazone 6c.Keywords - non-steroidal anti-inflammatory drugs / hydrazones / dual inhibitor / cyclooxygenase / lipoxygenase
