63012-03-3Relevant articles and documents
Tunable System for Electrochemical Reduction of Ketones and Phthalimides
Chen, Gong,Qiao, Tianjiao,Wang, Yaxin,Zhang, Jian,Zhao, Jianyou
supporting information, p. 3297 - 3302 (2021/10/14)
Herein, we report an efficient, tunable system for electrochemical reduction of ketones and phthalimides at room temperature without the need for stoichiometric external reductants. By utilizing NaN3 as the electrolyte and graphite felt as both the cathode and the anode, we were able to selectively reduce the carbonyl groups of the substrates to alcohols, pinacols, or methylene groups by judiciously choosing the solvent and an acidic additive. The reaction conditions were compatible with a diverse array of functional groups, and phthalimides could undergo one-pot reductive cyclization to afford products with indolizidine scaffolds. Mechanistic studies showed that the reactions involved electron, proton, and hydrogen atom transfers. Importantly, an N3/HN3 cycle operated as a hydrogen atom shuttle, which was critical for reduction of the carbonyl groups to methylene groups.
I2/Li2CO3-promoted cyanation of diarylalcohols through a dual activation process
Hu, Liangzhen,Hussain, Muhammad Ijaz,Deng, Qingfu,Liu, Qing,Feng, Yangyang,Zhang, Xiaohui,Xiong, Yan
, p. 308 - 314 (2018/12/11)
One-step base promoted strategy for cyanation of α,α-diaryl alcohols has been developed under mild and transition metal-free conditions. This method provides a straightforward and facile way towards the synthesis of β,γ-unsaturated nitriles and α-phenylnitiriles from α-vinyl carbinols and α,α-diaryl methanols, respectively, up to 99% yield. Moreover, various azides and ethers could also be accessed from their respective nucleophiles under standard reaction conditions.
One-pot synthesis of indene derivatives by CF3SO 3H-promoted reactions of benzylic alcohols and 1,3-dicarbonyl compounds
Zhang, Wei,Zhang, Wenxue,Dai, Yisi,Zhu, Haizhen
supporting information, p. 1747 - 1750 (2013/03/28)
An efficient and convenient one-pot synthesis of indene derivatives was achieved in moderate to high yields by the CF3SO3H promoted coupling/cyclization reaction of benzylic alcohols and 1,3-dicarbonyls for the first time. For the reactions of methoxy- or methyl-substituted diarylmethanols with 1,3-dicarbonyls, 2 equiv of CF3SO3H was needed to reach the best results; but for the reactions of methoxy-substituted arylethanols with 1,3-dicarbonyls, 0.6 equiv of CF 3SO3H at lower temperatures was capable of promoting the reaction finished.
Direct electrosynthesis of ketones from benzylic methylenes by electrooxidative C-H activation
Meng, Li,Su, Jihu,Zha, Zhenggen,Zhang, Li,Zhang, Zhenlei,Wang, Zhiyong
supporting information, p. 5542 - 5545 (2013/05/23)
Electrify your chemistry! Direct electrosynthesis of ketones from benzylic methylenes in an undivided cell was realized in moderate to good yields (see scheme). In this electrosynthesis, electrons instead of conventional oxidants and catalysts are employed to make the reaction environmentally benign. Moreover, the reaction intermediate radical was detected by ESR spectroscopy and the reaction mechanism was clarified.
Synthesis, antibacterial and antifungal activities of bifonazole derivatives
El Hage, Salome,Lajoie, Barbora,Feuillolay, Catherine,Roques, Christine,Baziard, Genevieve
experimental part, p. 402 - 410 (2012/01/11)
Two series of chlorinated benzhydryl imidazole and triazole derivatives were synthesized and tested in vitro against representative strains of potent pathogenic bacteria (Staphylococcus aureus CIP 4.83, Escherichia hirae CIP 5855, Pseudomonas aeruginosa CIP 82118, Escherichia coli CIP 53126) and fungi (Aspergillus niger IP 1431.83, Candida albicans IP 48.72, Candida krusei IP 208.52, Trichophython rubrum IP 1657.86). Most of these compounds were devoid of any antimicrobial activity, but several of them inhibited T. rubrum with MIC values in the range of 0.125 to 32 μg/mL, similar or superior to those of bifonazole and clotrimazole, used as standard controls. The replacement of the imidazole ring with a triazole moiety in these compounds led to derivatives with less antifungal activity. A preliminary SAR was undertaken on the effect of the number and the position of chlorine atoms on the distribution of negative charge on the surface of some compounds on antifungal activity. Copyright
Microwave-assisted nickel(II) acetylacetonate-catalyzed arylation of aldehydes with arylboronic acids
Chen, Wen,Baghbanzadeh, Mostafa,Kappe, C. Oliver
experimental part, p. 1677 - 1679 (2011/04/25)
Applying sealed vessel microwave heating at 180 °C in toluene the arylation of aromatic and aliphatic aldehydes with arylboronic acids using 1-2 mol % of Ni(acac)2 as a catalyst can be performed efficiently within 10-30 min providing the desired diarylmethanols or benzyl alcohols in good yields.
Ni(COD)2/4-ClC6H4COR-catalyzed addition reactions of arylboroxines with aldehydes
Xing, Chun-Hui,Hu, Qiao-Sheng
supporting information; experimental part, p. 924 - 927 (2010/05/18)
Ni(COD)2/4-ClC6H4COR (R = H, CH3, Ph) was found to be an efficient catalyst system for the addition reactions of arylboroxines with aromatic and aliphatic aldehydes. The catalytically active species for Ni(COD)2/4-ClC6H4COR catalyst systems was likely to be their oxidative addition adducts, 4-RCOC6H4Ni(II)Cl(COD) complexes.
Structure-activity relationships of diphenylpiperazine N-type calcium channel inhibitors
Pajouhesh, Hassan,Feng, Zhong-Ping,Ding, Yanbing,Zhang, Lingyun,Pajouhesh, Hossein,Morrison, Jerrie-Lynn,Belardetti, Francesco,Tringham, Elizabeth,Simonson, Eric,Vanderah, Todd W.,Porreca, Frank,Zamponi, Gerald W.,Mitscher, Lester A.,Snutch, Terrance P.
scheme or table, p. 1378 - 1383 (2010/07/06)
A novel series of compounds derived from the previously reported N-type calcium channel blocker NP118809 (1-(4-benzhydrylpiperazin-1-yl)-3,3-diphenylpropan-1-one) is described. Extensive SAR studies resulted in compounds with IC50 values in the range of 10-150 nM and selectivity over the L-type channels up to nearly 1200-fold. Orally administered compounds 5 and 21 exhibited both anti-allodynic and anti-hyperalgesic activity in the spinal nerve ligation model of neuropathic pain.
A metal-free catalytic system for the oxidation of benzylic methylenes and primary amines under solvent-free conditions
Zhang, Jintang,Wang, Zhentao,Wang, Ye,Wan, Changfeng,Zheng, Xiaoqi,Wang, Zhiyong
supporting information; scheme or table, p. 1973 - 1978 (2010/06/15)
Iodine-pyridine-tert-butylhydroperoxide is developed as a green and efficient catalytic system for the oxidation of benzylic methylenes to ketones and primary amines to nitriles. The reaction conditions are quite mild and environmentally benign, no transition metals, organic solvents or hazard reagents being needed. The oxidation of benzylic methylenes gave the corresponding ketones in excellent yields with complete chemoselectivity, while the oxidation of primary amines was complete in several minutes, affording various nitriles in moderate to good yields.
Copper-catalyzed synthesis of enantioenriched tetraarylethanes
Jen, Wendy S.,Truppo, Matthew D.,Amos, Deborah,Devine, Paul,McNevin, Michael,Biba, Mirlinda,Campos, Kevin R.
supporting information; experimental part, p. 741 - 744 (2009/04/06)
Herein we report the asymmetric synthesis of 1,2-dipyridyl-1,2- diarylethanes via an unusual Cu(l)-catalyzed dimerization reaction. Subjection of a variety of enantioenriched substituted 2-pyridyl alcohols to a one-pot protocol generates the desired products in good yields and diastereoselectivities and with ee's up to >99%.
