Synthesis of 2-acetyl trisubstituted furans via copper-mediated deacylation cleavage of unstrained C(sp3)–C(sp2) bonds
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A copper-mediated tandem addition/cyclization/carbon–carbon cleavage reaction for the convenient synthesis of 2-acyl trisubstituted furans has been developed.Keywords:
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The metathetical reaction between cis-RuCl2(PMe3)4 and an excess amount of potassium 2,6-dimethylphenoxide rapidly produces an oxaruthenacycle by the sp3 C–H bond cleavage reaction of the o-methyl group. With potassium 2,6-diethyl- and 2,6-diisopropylphenoxides, multiple C–H bond cleavage of o-alkyl groups occurs to give unsaturated oxaruthenacycles. These multiple activations are triggered by the sp3 C–H bond cleavage of the o-alkyl group from bis(2,6-dialkylphenoxo)ruthenium(II) to form a saturated ruthenacycle followed by β-hydride elimination and dehydrogenation from the resulting (2-alkenyl-6-alkylphenoxo)(hydrido)ruthenium(II) intermediate.
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Abstract A palladium‐catalyzed desulfitative coupling of quinoxalin‐2(1 H )‐ones with arylsulfonyl chlorides is described. C3‐Arylquinoxalin‐2(1 H )‐ones are readily accessible by reacting various arylsulfonyl chloride derivatives with quinoxalin‐2(1H)‐ones. The arylsulfonyl chloride undergoes palladium‐catalyzed C−S and S−Cl bond cleavage, which leads to direct desulfitative cross‐coupling with the quinoxalin‐2( H )‐one. Chloro‐ and fluoro‐aryl sulfonyl chlorides are successfully coupled with quinoxalin‐2(1 H )‐ones without carbon–halogen bond cleavage.
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Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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Abstract A new type of three‐component reaction to achieve the synthesis of a series of N‐ethoxymethylated heterocyclic compounds in high regioselectivity is reported.
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Reactions of the yttrium anilido hydride [LY(NH(DIPP))(μ-H)]2 (1; L = [MeC(N(DIPP))CHC(Me)(NCH2CH2NMe2)]−, DIPP = 2,6-iPr2C6H3)) with three phosphine oxides and two phosphine sulfides are reported. The reaction of 1 with Ph3P═O gives C–P bond cleavage and an yttrium anilido phosphinoyl complex, while those with R2MeP═O (R = Me, Ph) result in C–H bond cleavage and two yttrium anilido alkyl complexes. 1 also reacted with R3P═S (R = Me, Ph), which demonstrated P–S bond cleavage via hydride-based reduction and gave an yttrium anilido sulfide.
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Abstract The reaction of allyl phenyl or methyl sulfide with Ru(cod)(cot) (1) [cod: 1,5-cyclooctadiene, cot: 1,3,5-cyclooctatriene] in the presence of depe [1,2-bis(diethylphosphino)ethane] causes cleavage of the allyl sulfur bond to afford the cationic π-allyl ruthenium complex, [Ru(η3-C3H5)(depe)2)] [RS] (R = Ph, 2; Me, 3). The thiolate anion is easily exchanged by treatment with NaBPh4.
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Methyl P-bromomethyl-N-tert-butylphosphonamidate 10 (R = Me) rearranges with methoxide, giving dimethyl tert-butylaminomethylphosphonate 12 (R = R′ = Me) and dimethyl N-tert-butyl-N-methylphosphoramidate 13 (R = R′ = Me) in comparable amounts. These products are derived from the (postulated) azaphosphiridine oxide intermediate 11 (R = Me) by nucleophilic attack at phosphorus and cleavage of the P–N or P–C bond. Increased bulk in the alkyl group of the alkoxy ligand (R = methyl < cyclohexyl < tert-butyl < menthyl) or the alkoxide nucleophile (methoxide < tert-butoxide) increases P–N bond cleavage at the expense of P–C cleavage.
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Propargyl bromide
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GilOII has been unambiguously identified as the key enzyme performing the crucial C-C bond cleavage reaction responsible for the unique rearrangement of a benz[a]anthracene skeleton to the benzo[d]naphthopyranone backbone typical of the gilvocarcin-type natural anticancer antibiotics. Further investigations of this enzyme led to the isolation of a hydroxyoxepinone intermediate, leading to important conclusions regarding the cleavage mechanism.
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The syntheses of a group of 2-(o-nitrophenyl)- and 2-(o-aminophenyl)-5,8-quinolinediones which are structurally related to the antitumor antibiotic streptonigrin are described. Ambiguities in the position of required nucleophilic displacements are resolved by independent synthesis. The rates of single strand cleavage of PM2 ccc-DNA (covalently-closed circular-DNA) induced by these compounds are compared, which correlates with antitumor activity. The 2-(o-nitrophenyl) derivatives give consistently more rapid DNA cleavage than the 2-(o-aminophenyl) compounds. The autoxidations of the dihydroxyquinolines are subject to selective catalysis by Cu 2+ on. 2-(o-Aminophenyl)-7-amino-6-methoxy-5,6-quinolinedione which has a substitution pattern most closely resembling streptonigrin also closely parallels the rate of scission of DNA of the latter in the presence of NADPH.
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