14252-32-5Relevant articles and documents
SYNTHESIS IF ACETYLENIC KETONES FROM THIOL ESTERS AND 1-ALKYNYLTRIMETHYLSILANES
Kawanami, Yasuhiro,Katsuki, Tsutomu,Yamaguchi, Masaru
, p. 5131 - 5132 (1983)
In the presence of silver tetrafluoroborate, S-ethyl carbothioates reacted with 1-alkynyltrimethylsilanes to give the corresponding acetylenic ketones in good yields.
Mild propargylic oxidation using a diacetoxyiodobenzene/tert-butyl hydroperoxide protocol
Zhao, Yi,Ng, Angela Wan Ting,Yeung, Ying-Yeung
, p. 4370 - 4372 (2014)
A mild propargylic oxidation of alkynes is reported using a diacetoxyiodobenzene/tert-butyl hydroperoxide (DIB/TBHP) protocol. The reactions proceed smoothly at 0 °C and a number of α,β-unsaturated alkynoic ketones are obtained.
Alkynylation of aldehydic C-H bonds via reaction with acetylenic triflones.
Gong, Jianchun,Fuchs
, p. 787 - 790 (1997)
Reaction of aldehydes with acetylenic triflones affords acetylenic ketones and alkylated acetylenes via the intermediacy of acyl radicals, the product ratio being highly dependent upon aldehyde structure and reaction conditions.
Fine-tuning dirhodium compounds with bridging ligands: Synthesis, structure, catalytic efficiency
Ning, Yangbo,Tan, Jiantao,Wang, Yuanhua,Wang, Zhifan
supporting information, (2021/09/28)
The structure of dirhodium compounds contains a unique Rh-Rh bond, two axial ligands and four bridging ligands. In the dirhodium(II) compounds, it is easy to migrate the coordinating atoms of the bridging ligand during the catalysis process, which leads to the degradation of the catalyst. Coordination atom migration was identified in bridging ligands. To improve the catalyst stability, we carried out a study on the effect of fine-tuning of the bridging ligand on the dirhodium compound. Several dirhodium compounds were designed and synthesized. During this process, we have successfully found Rh2(5-Br-esp)2 and Rh2(5-tBu-esp)2, which are closer to the ideal geometric configuration of the dirhodium(II) compounds. Rh2(5-Br-esp)2 has been applied in the oxidation of propargyl position and Rh2(5-tBu-esp)2 in the formation reaction of the C–N bond.
Synthesis of substituted benzo[: B] [1,4]oxazepine derivatives by the reaction of 2-aminophenols with alkynones
Oshimoto, Kohei,Zhou, Biao,Tsuji, Hiroaki,Kawatsura, Motoi
supporting information, p. 415 - 419 (2020/01/30)
We have developed a novel synthetic method accessing benzo[b][1,4]oxazepines that are one of the rare classes of benzoxazepine derivatives by reaction of 2-aminophenols with alkynones in 1,4-dioxane at 100 °C. A series of benzo[b][1,4]oxazepine derivatives can be prepared by using this synthetic protocol. Mechanistic experiments indicated that the hydroxy proton of the aminophenol could play a crucial role in the formation of an alkynylketimine intermediate that undergoes 7-endo-dig cyclization.
Catalytic Ynone-Amidine Formal [4 + 2]-Cycloaddition for the Regioselective Synthesis of Tricyclic Azepines
Reddy, T. Prabhakar,Gujral, Jagjeet,Roy, Pritam,Ramachary, Dhevalapally B.
supporting information, p. 9653 - 9657 (2021/01/09)
A Ca(OTf)2- and self-promoted ynone-amidine atom-economic formal [4 + 2]-cycloaddition of various ynones with amidines is reported for the construction of highly functionalized tricyclic azepines. High reaction rate, ease of operation, and high product se
Intramolecular and Ferrier Rearrangement Strategy for the Construction of C1-β-d-xylopyranosides: Synthesis, Mechanism and Biological Activity Study
Yao, Yuan,Xiong, Cai-Ping,Zhong, Ya-Ling,Bian, Guo-Wei,Huang, Nian-Yu,Wang, Long,Zou, Kun
supporting information, p. 1012 - 1017 (2019/01/30)
A stereoselective synthesis of C1-β-d-xylopyranoside derivatives had been developed via intramolecular 1,3-acyloxy migration/Ferrier rearrangement stategy from readily available propargylic carboxylates and d-xylal. A combined catalytic system of chloro(t
Rhodium-Catalyzed Intermolecular trans-Disilylation of Alkynones with Unactivated Disilanes
He, Tao,Liu, Li-Chuan,Guo, Le,Li, Bin,Zhang, Qing-Wei,He, Wei
supporting information, p. 10868 - 10872 (2018/07/31)
Disilylation of alkynes could provide rapid entry to synthetically useful 1,2-bissilyl-alkenes, but is currently limited to activated disilanes reacting in an intramolecular fashion. Reported herein is an efficient rhodium(I)-catalyzed intermolecular disi
Highly regioselective gold-catalyzed formal hydration of propargylic: Gem -difluorides
Hamel, Jean-Denys,Hayashi, Tatsuru,Cloutier, Mélissa,Savoie, Paul R.,Thibeault, Olivier,Beaudoin, Meggan,Paquin, Jean-Fran?ois
supporting information, p. 9830 - 9836 (2017/12/08)
Herein, we report a highly regioselective gold-catalyzed formal hydration of propargylic gem-difluorides. Not only does this transformation provide access to versatile fluorinated building blocks that were difficult or hardly possible to access beforehand, but it also represents a rare case of a highly regioselective gold-catalyzed hydroalkoxylation of internal alkynes and puts forward the utility of the difluoromethylene unit as a directing group in catalysis.
Ferrocenyl, Alkyl, and Aryl-Pyrido[2,3-d]Pyrimidines as Vasorelaxant of Smooth Muscle of Rat Aorta via cAMP Conservation Through Phosphodiesterase Inhibition
Arellano, Ivonne,Rodríguez-Ramos, Fernando,González-Andrade, Martín,Navarrete, Andrés,Sharma, Manju,Rosas, Noé,Sharma, Pankaj
, p. 1147 - 1154 (2016/07/29)
New pyrido[2,3-d]pyrimidines 11, 12, 13, and 21 have been synthesized. The vasorelaxant effect on smooth muscle isolated from rat aorta, via PDEs inhibition, of these compounds along with other pyrido[2,3-d]pyrimidines 14, 15, 16, 17, 18, 19, 20 reported earlier by our group, has also been determined. These pyrido[2,3-d]pyrimidines 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 were synthesized by the reaction of ferrocenyl-ethynyl ketones (1, 2, 3, 4) or α-alkynyl ketones (5, 6, 7, 8, 9, 10) with 6-amino-1,3-dimethyluracil using [Ni(CN)4]?4as an active catalytic species, formed in situ in a Ni(CN)2/NaOH/H2O/CO/KCN aqueous system. Evaluation of the vasorelaxant effect of compounds 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 demonstrated that all compounds relax the tissue in a concentration-dependent manner. The structural changes do not alter the effectiveness; however, there are differences related to potency expressed as EC50. Compounds 12 (7-ferrocenyl-1,3-dimethyl-5-(m-tolyl)-pyrido[2,3-d]pyrimidine) and 13 (7-ferrocenyl-1,3-dipropyl-5-(4-metoxyphenyl)-pyrido[2,3-d]pyrimidine) were the most potent compounds, even more than rolipram, reference drug; the EC50was 0.41 ± 0.02 μM and 0.81 ± 0.11 μM for 12 and 13, correspondingly. The EC50of compounds 15 (7-ferrocenyl-1,3-dimethyl-5-phenyl-pyrido[2,3-d]pyrimidine), 14 (7-ferrocenyl-5-(3,5-dimethoxyphenyl)-1,3-dimethylpyrido[2,3-d]pyrimidine), and 19 (5-n-butyl-7-ethyl-1,3-dimethylpyrido[2,3-d]pyrimidine) was similar to EC50of rolipram. Compounds 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 significantly induce concentration-dependent vasorelaxation in endothelium-intact aortic rings. In addition, the relaxation responses to each compound in either endothelium-intact or endothelium denuded aortic rings were comparable, suggesting that removal of the functional endothelium has no significant influence on its intrinsic vasorelaxant activity. In vitro capability of conserving cyclic-AMP or cyclic-GMP (adenosine and guanosine 3′, 5′-cyclic monophosphate) via PDE inhibition for compounds 12, 13, 14, 15 and 19 was evaluated. Compounds 15 and 19 show the highest percent inhibition effect (94.83% and 83.98%, respectively) for the decomposition of c-AMP. Docking studies showed that the compound 15 was selective for the inhibition of PDE-4.
