- Tandem catalytic C(sp3)-H amination/sila-sonogashira-hagihara coupling reactions with iodine reagents
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A new tandem C-N and C-C bond-forming reaction has been achieved through RhII/Pd0 catalysis. The sequence first involves an iodine(III) oxidant, then the in situ generated iodine(I) by-product is used as a coupling partner. The overall process demonstrates the synthetic value of iodoarenes produced in trivalent iodine reagent mediated oxidations. I(003) is a double agent: A tandem C-N and C-C bond-forming reaction has been achieved through RhII/Pd0 catalysis. The sequence first involves an iodine(III) oxidant, then the in situ generated iodine(I) by-product is used as a coupling partner. The overall process affords complex building blocks with high yields, and demonstrates the synthetic value of iodoarenes produced in trivalent iodine reagent mediated oxidations.
- Buendia, Julien,Darses, Benjamin,Dauban, Philippe
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p. 5697 - 5701
(2015/06/16)
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- Role of sterically demanding chiral dirhodium catalysts in site-selective C-H functionalization of activated primary C-H bonds
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The influence of sterically demanding dirhodium tetracarboxylate catalysts on the site selectivity of C-H functionalization by means of rhodium carbene-induced C-H insertion is described. The established dirhodium tetraprolinate-catalyzed reactions of aryldiazoacetates cause preferential C-H functionalization of secondary C-H bonds as a result of competing steric and electronic effects. The sterically more demanding dirhodium tetrakis(triarylcyclopropanecarboxylate) catalysts, exemplified by dirhodium tetrakis[(R)-(1-(biphenyl)-2,2-diphenylcyclopropanecarboxylate)] [Rh 2(R-BPCP)4], favor C-H functionalization of activated primary C-H bonds. Highly site-selective and enantioselective C-H functionalization of a variety of simple substrates containing primary benzylic, allylic, and methoxy C-H bonds was achieved with this catalyst. The utility of this approach has been demonstrated by the late-stage primary C-H functionalization of (-)-∝-cedrene and a steroid.
- Qin, Changming,Davies, Huw M. L.
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p. 9792 - 9796
(2014/07/22)
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- Process for Producing Aromatic Aldehyde Compound
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A process for producing an aromatic aldehyde compound has steps of converting alkyl-substituted or non-substituted benzene into a compound of formula I by halomethylation, and allowing the compound of formula I and alkyl aldehyde to react in presence of phase transfer catalyst at a reaction temperature under alkaline condition to obtain the aromatic aldehyde compound.
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Page/Page column 4
(2012/10/23)
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- Discovery and development of thiazolo[3,2-a]pyrimidinone derivatives as general inhibitors of Bcl-2 family proteins
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A class of compounds with a common thiazolo[3,2-a]pyrimidinone motif has been developed as general inhibitors of Bcl-2 family proteins. The lead compound was originally identified in a random screening of a small compound library using a fluorescence polarization-based competitive binding assay. Its binding to the Bcl-xL protein was further confirmed by 15N-HSQC NMR experiments. Structural modifications on the lead compound were guided by the outcomes of molecular modeling studies. Among the 42 compounds obtained, a number of them exhibited much improved binding affinities to Bcl-2 family proteins as compared to the lead compound. The most potent compound, BCL-LZH-40, inhibited the binding of BH3 peptides to Bcl-xL, Bcl-2, and Mcl-1 with inhibition constants (Ki) of 17, 534, and 200nM, respectively. Keeping it in the family! Compounds with a common thiazolo[3,2-a]pyrimidinone motif have been developed as general inhibitors of Bcl-2 family proteins. The lead compound BCL-LZH-01 (shown in green) was identified as a Bcl-xL protein binder in a random screening using a fluorescence polarization-based binding assay, and further confirmed by 15N-HSQC NMR experiments. Of the 42 derivative described, BCL-LZH-40 (shown in blue) is the most potent, inhibiting the binding of BH3 peptides to Bcl-xL, Bcl-2, and Mcl-1 with inhibition constants (Ki) of 17, 534, and 200nM, respectively.
- Zhou, Bingcheng,Li, Xun,Li, Yan,Xu, Yaochun,Zhang, Zhengxi,Zhou, Mi,Zhang, Xinglong,Liu, Zhen,Zhou, Jiahai,Cao, Chunyang,Yu, Biao,Wang, Renxiao
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p. 904 - 921
(2012/01/06)
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- Making a difference on excited-state chemistry by controlling free space within a nanocapsule: Photochemistry of 1-(4-alkylphenyl)-3-phenylpropan-2-ones
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The free space within a reaction cavity plays a determining role during the excited-state reaction of 1-(4-alkylphenyl)-3-phenylpropan-2-ones included within a capsule formed by two molecules of a deep cavity cavitand. By controlling the free space within the reaction cavity through remote alkyl substitution on the reactant ketone it is possible to control the yield of the rearrangement product shown above.
- Sundaresan, Arun Kumar,Ramamurthy
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p. 3575 - 3578
(2008/02/12)
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- An efficient synthesis of benzyl bromides from aromatic aldehydes using polymethylhydrosiloxane and (bromodimethyl)sulfonium bromide or N-bromosuccinimide
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Polymethylhydrosiloxane (PMHS) in combination with (bromodimethyl)sulfonium bromide or NBS has been utilized for the first time for reductive bromination of aromatic aldehydes at room temperature to afford the corresponding benzyl bromides in excellent yields.
- Das, Biswanath,Srinivas, Yallamalla,Holla, Harish,Laxminarayana, Keetha,Narender, Ravirala
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p. 6681 - 6683
(2008/03/12)
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- Bromomethylation of aromatics mediated by low frequency ultrasound
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We report herein bromomethylation of aromatics mediated by low frequency ultrasound to yield bromomethylated aromatic rings which are useful synthetic intermediates.
- Khurana, Jitender M.,Maikap, Golak C.
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p. 216 - 217
(2007/10/03)
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- Coumarin derivative and use thereof
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The present invention provides compounds having 12-lipoxygenase inhibitory effect and medicines inhibiting 12-lipoxygenase selectively, and relates to novel coumarin derivatives and medicines containing the compounds as effective ingredients. Furthermore,
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- Stilbene derivative and stilbene analog derivative, and use thereof
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The present invention relates to a novel compound having a 12-lipoxygenase inhibitory effect, of the general formula (I), a precursor thereof, and a medicine containing the same, STR1 wherein R1 represents a hydrogen atom or a hydroxy group; on
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- Reactions in Microemulsion Media. Nucleophilic Substitution Reactions of Benzyl and p-Alkylbenzyl Chlorides
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A kinetic and synthetic study of nucleophilic displacement reaction of bromide ion with benzyl chloride (1a) and its p-ethyl-substituted (1b) and p-n-dodecyl-substituted (1c) analogues has been performed in microemulsions prepared from combinations of a 1.23:1 (w/w) mixture (S) of cetyltrimethylammonium bromide (CTABr) and 1-butanol, a 1:5 (w/w) KBr-H2O solution (W), and hexane (O).The rates of reaction decreased differentially with increasing hexane content at a constant ratio of S:W to indicate that the interphase was the microemulsion reactive site.For microemulsion with respect to aqueous micellar and aqueous ethanol reaction media, solubilization of substrate was higher, initial reaction rates were comparable or slightly less, and overall conversions were greater.
- Martin, Craig A.,McCrann, Patrick M.,Ward, Mary Darlene,Angelos, George H.,Jaeger, David A.
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p. 4392 - 4396
(2007/10/02)
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- REACTIVITE DES GEM-DIBROMOCYCLOPROPANES-IV; OUVERTURE ACIDO-CATALYSEE DE GEM-DIHALOGENOCYCLOPROPYLCARBINOLS
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By acid catalysis, gem-dihalogenocyclopropylcarbinols are converted into homoallylic α-dihalogenated cations which in general eliminate the hydrogen halide and lead to the 3-halogenopentadienyl cations from which cyclopentenones can be formed by cyclisation.For bicycloheptanes, aromatisation of the 3-halogenopentadienyl cation in benzyl bromide is observed.
- Santelli-Rouvier, Christiane
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p. 4195 - 4200
(2007/10/02)
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