- Thiocyanation and 2-Amino-1,3-thiazole Formation in Water Using Recoverable and Reusable Glycosylated Resorcin[4]arene Cavitands
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A family of three spatially directional resorcin[4]arene cavitand glycoconjugates (RCGs) have been applied as efficient recoverable and reusable inverse phase transfer catalysts for eco- A nd environmentally friendly thiocyanation and 2-amino-1,3-thiazole formation reactions in water. The results show that RCGs (1 mol %) were capable of hosting and catalyzing various water-insoluble bromo/thiocyanato substrates in water without the use of any co-organic solvents. The recoverability and reusability of RCG catalytic systems, that is, RCG1 and RCG3, were also examined upon a simple extraction of the desired products using DCM or ethyl acetate, followed by subjecting the recovered aqueous solution containing the RCG catalysts to the next reaction cycles.
- Husain, Ali A.,Bisht, Kirpal S.
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p. 9928 - 9935
(2020/09/03)
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- Eosin-Mediated Alkylsulfonyl Cyanation of Olefins
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Eosin-Y (EY)-mediated alkylsulfonyl cyanation of olefins was shown to afford alkylsulfonyl nitriles in good yields. On the basis of transient absorption spectroscopy, the reaction was shown to proceed via photoinduced electron transfer from 3EY? to an O-cyanated derivative of the photocatalyst, formed in situ, with generation of the corresponding sulfinate that is oxidized by EY?.+ into a sulfonyl radical. Addition of the latter on the olefin, followed by a radical cyano group transfer, then furnished the nitrile along with a RSO2 radical sustaining the radical chain.
- Pirenne, Vincent,Kurtay, Gülbin,Voci, Silvia,Bouffier, Laurent,Sojic, Neso,Robert, Frédéric,Bassani, Dario M.,Landais, Yannick
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supporting information
p. 4521 - 4525
(2018/08/09)
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- Free-Radical Carbocyanation of Olefins
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The free-radical three-component carbocyanation of electron-rich olefins was investigated with p-tosyl cyanide as cyanide source. The scope and limitations of the process were established by varying the nature of the alkene and radical precursor. Carbocyanation of chiral allylsilanes was shown to occur with high diastereocontrol, leading to syn β-silyl nitriles. The origin of the stereocontrol was rationalized by a Felkin–Anh-type transition-state model. Finally, a tin-free carbocyanation process was also devised, based on the use of a new alkylsulfonyl cyanide incorporating both carbon fragments to be added across the olefinic π system.
- Hassan, Haitham,Pirenne, Vincent,Wissing, Maren,Khiar, Chahinaz,Hussain, Ashique,Robert, Frédéric,Landais, Yannick
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supporting information
p. 4651 - 4658
(2017/04/13)
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- Ionic liquid brush as a highly efficient and reusable catalyst for on-water nucleophilic substitutions
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A very efficient and reusable catalyst has been developed for the on-water nucleophilic substitution of alkyl halides and tosylates with azide or thiocyanate in excellent to quantitative yields. The reaction proceeds smoothly and cleanly without any organic cosolvent or other adductive, and the brush can be reused at least 10 times without noticeable loss of the catalytic activity. The high efficiency, simplicity of product and catalyst isolation, outstanding recyclability, and organic-solvent-free conditions show promise for the use of this catalyst in the laboratory and in industry. A highly efficient and reusable ionic liquid brush catalyst has been developed for the on-water nucleophilic substitution of alkyl halides and tosylates with azide or thiocyanate in excellent to quantitative yields without any organic cosolvent or other adductive. The catalyst can be reused at least 10 times without noticeable loss of the catalytic activity. Copyright
- Li, Jing,Cao, Jing-Jing,Wei, Jun-Fa,Shi, Xian-Ying,Zhang, Li-Hui,Feng, Jin-Juan,Chen, Zhan-Guo
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supporting information; experimental part
p. 229 - 233
(2011/03/20)
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- Thiazolinone 2-substituted quinolines
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Thiazolinone substituted quinoline derivatives where the quinoline ring is substituted at the 2 position which derivatives demonstrates CDK1 antiproliferative activity and are useful as anti-cancer agents.
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Page/Page column 14
(2010/10/20)
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- Thiazolinone unsubstituted quinolines
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Thiazolinone quinoline derivatives having no substitution on the quinoline ring active as CDK1 inhibitors which are useful as anti-proliferation agents such as for treating solid tumors.
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Page/Page column 28
(2010/02/15)
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- Preparation of New Nitrogen-Bridged Heterocycles. 42.1 Synthesis and the Reaction of Pyridinium N-Ylides Using Bifunctional Ethyl Thiocyanatoacetates
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Various pyridinium (monosubstituted methylide)s were smoothly attacked to the cyano group in ethyl thiocyanatoacetate or ethyl 2-thiocyanatopropionate to afford the corresponding pyridinium (substituted cyanomethylide)s in low-to-moderate yields, while pyridinium (unsubstituted amidate)s reacted with the ester carbonyl group in the same reagents to give pyridinium (thiocyanatoaceto)- or (2-thiocyanatopropiono)amidates in considerable yields. The 1,3-dipolar cycloadditions of some pyridinium (unsymmetrically substituted cyanomethylide)s with dimethyl acetylenedicarboxylate (DMAD) in various solvents afforded only dimethyl 3-cyanoindolizine-1,2-dicarboxylate, except a few examples. On the other hand, the treatment of pyridinium (thiocyanatoaceto)- or (2-thiocyanatopropiono)amidates with a strong base, such as potassium t-butoxide, gave new bicyclic mesoionic compounds, N-[2-(1,3,4-thiadiazolo(3,2-a]pyridinio)]acetamidate derivatives, in moderate yields. The intermediacy of N-[1-(2-thiocyanatopyridinio)]acetamidates in the formation reactions of the latter compounds was also proven by independent syntheses.
- Kakehi, Akikazu,Ito, Suketaka,Hashimoto, Yasunobu
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p. 1769 - 1776
(2007/10/03)
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- 1,3-Oxazines and Related Compounds. IX. Alkylation, Acylation, and Cleavage Reaction of 6-Methyl-4-oxo-2-thioxo-3,4-dihydro-2H-1,3-oxazine
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Alkylation of the title compound (2) with alkyl halides in the presence of Et3N proceeded exclusively on the sulfur atom to give the alkyl-1,3-oxazine derivatives.Acylation with acyl chlorides took place regioselectively on the nitrogen atom, giving the N-acyl derivatives. 1,3-Oxazine 2 was found to undergo cleavage of the ring into acetylketene and thiocyanic acid.Hence, treatment of 2 with alkyl halides in the presence of K2CO3 gave alkyl thiocyanates; treatment with active methylene compounds afforded γ-pyrone derivatives.N-Acyl derivatives of 2 also underwent thermal cleavage of the ring, leading to the corresponding acyl isothiocyanates.Keywords - 2-thioxo-4-oxo-1,3-oxazine; acetylketene; thiocyanic acid; acyl isothiocyanate; alkyl thiocyanate; acylation; alkylation; substituted γ-pyrone.
- Yamamoto, Yutaka,Morita, Yasuo
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p. 2957 - 2962
(2007/10/02)
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