- First total synthesis of a novel amide alkaloid derived from Aconitum taipeicum and its anticancer activity
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A concise total synthesis of a naturally occurring 3-isopropyl-tetrahydropyrrolo[1, 2-a]pyrimidine-2, 4(1H, 3H)-dione (ITPD) isolated from Aconitum taipeicum with a three-step approach was depicted in this study for the first time. Two key intermediates, diethyl isopropylmalonate (2) and pyrrolidin-2-amine (3), being synthsesised separately from initial diethyl malonate (4) and 3, 4-dihydro-2H-pyrrol-5-amine (5), were utilised to obtain the compound entitled ITPD. ITPD showed a promising anticancer activity in vitro on SMMC-7721 cell lines. Flow cytometry and cell cycle analysis revealed that ITPD could induce apoptosis and cell cycle arrest in S phase. The occurrence of apoptosis possibly attributed to the mechanism that ITPD could mediate the mitochondrial pathway through activating caspase-3/9 and increasing the ratio of Bax/Bcl-2 to finally trigger cell apoptosis and DNA damage. Collectively, the possibility to produce sufficient quantity of synthetic ITPD provided the base for further bio-evaluation in vivo and in vitro. The bioactive assay suggested that it may be a potential candidate for further chemical optimisation and use in cancer therapy.
- Zhang, Xinxin,Li, Dandan,Xue, Xuanji,Zhang, Yan,Zhang, Jie,Huang, Chen,Guo, Zengjun,Tadesse, Nigatu
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Read Online
- Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)
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The use of mono-substituted malonic acid half oxyesters (SMAHOs) has been hampered by the sporadic references describing their preparation. An evaluation of different approaches has been achieved, allowing to define the best strategies to introduce diversity on both the malonic position and the ester function. A classical alkylation step of a malonate by an alkyl halide followed by a monosaponification gave access to reagents bearing different substituents at the malonic position, including functionalized derivatives. On the other hand, the development of a monoesterification step of a substituted malonic acid derivative proved to be the best entry for diversity at the ester function, rather than the use of an intermediate Meldrum acid. Both these transformations are characterized by their simplicity and efficiency, allowing a straightforward access to SMAHOs from cheap starting materials.
- Condon, Sylvie,Le Gall, Erwan,Pichon, Christophe,Presset, Marc,Xavier, Tania
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supporting information
p. 2085 - 2094
(2021/09/02)
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- Synthesis of Cyclopentenones through Rhodium-Catalyzed C-H Annulation of Acrylic Acids with Formaldehyde and Malonates
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An efficient rhodium-catalyzed protocol for the synthesis of cyclopentenones based on a three-component reaction of acrylic acids, formaldehyde, and malonates via vinylic C-H activation is reported. Exploratory studies showed that 5-alkylation of as-prepared cyclopentenones could be realized smoothly by the treatment of a variety of alkyl halides with a Na2CO3/MeOH solution. Excess formaldehyde and malonate led to a multicomponent reaction that afforded the multisubstituted cyclopentenones through a Michael addition.
- Yu, Shuling,Hong, Chao,Liu, Zhanxiang,Zhang, Yuhong
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supporting information
p. 5054 - 5059
(2021/07/20)
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- Regiospecific S-aminoalkylation of 5-substituted 6-hydroxy-2-thiouracil derivatives in the synthesis of structural analogs of isothiobarbamine
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Regiospecific S-monoaminoalkylation of 5-substituted derivatives of 6-hydroxy-2-thiouracil with free N,N-dialkyl-N-(2-chloroethyl)amines in anhydrous PriOH was described for the first time. In compliance with the rules and regulations of green chemistry, this approach was used to synthesize a number of structural analogs of isothiobarbamine in high yield and purity, which are potential synthetic actoprotectors of immediate action.
- Brunilina, L. L.,Chapurkin, V. V.,Deshevov, P. P.,Kirillov, I. A.,Korenkov, B. D.,Nawrozkij, M. B.,Novakov, I. A.,Sheikin, D. S.,Vostrikova, O. V.
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p. 943 - 948
(2021/06/07)
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- Silylene-Bridged Tetranuclear Palladium Cluster as a Catalyst for Hydrogenation of Alkenes and Alkynes
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A planar tetranuclear palladium cluster was obtained from the reaction of a cyclotetrasilane with [Pd(CNtBu)2]3. Single-crystal X-ray diffraction analysis and DFT calculations revealed that the tetranuclear framework of the cluster was supported effectively by the bridging organosilylene ligand. Although [Pd(CNtBu)2]3 as well as mononuclear palladium bis(silyl) complex, cis-Pd(SiMePh2)2(CNtBu)2, do not act as the effective catalyst, the planar tetranuclear palladium cluster acts as an efficient catalyst for the hydrogenation of alkenes and alkynes including sterically hindered tri- and tetra-substituted alkenes.
- Yanagisawa, Chikako,Yamazoe, Seiji,Sunada, Yusuke
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p. 169 - 173
(2020/10/29)
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- Nuclearity expansion in Pd clusters triggered by the migration of a phenyl group in cyclooligosilanes
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Heptanuclear palladium clusters with six palladium atoms in a planar arrangement were obtained from the reaction of [Pd(CNtBu)2]3with Ph-substituted cyclotetrasilane or cyclopentasilaneviathe migration of a phenyl group. The molecular structures of these clusters as well as those of two possible intermediates were determined by single-crystal X-ray diffraction analyses.
- Shimamoto, Kento,Sunada, Yusuke
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supporting information
p. 7649 - 7652
(2021/08/09)
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- General access to C-centered radicals: Combining a bioinspired photocatalyst with boronic acids in aqueous media
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Carbon-centered radicals are indispensable building blocks for modern synthetic chemistry. In recent years, visible light photoredox catalysis has become a promising avenue to access C-centered radicals from a broad array of latent functional groups, including boronic acids. Herein, we present an aqueous protocol wherein water features a starring role to help transform aliphatic, aromatic, and heteroaromatic boronic acids to C-centered radicals with a bioinspired flavin photocatalyst. These radicals are used to deliver a diverse pool of alkylated products, including three pharmaceutically relevant compounds, via open-shell conjugate addition to disparate Michael acceptors. The mechanism of the reaction is investigated by computational studies, deuterium labeling, radical-trapping experiments, and spectroscopic analysis.
- Bloom, Steven,Chilamari, Maheshwerreddy,Immel, Jacob R.
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p. 12727 - 12737
(2020/11/18)
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- Dehydroxymethylation of alcohols enabled by cerium photocatalysis
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Dehydroxymethylation, the direct conversion of alcohol feedstocks as alkyl synthons containing one less carbon atom, is an unconventional and underexplored strategy to exploit the ubiquity and robustness of alcohol materials. Under mild and redox-neutral reaction conditions, utilizing inexpensive cerium catalyst, the photocatalytic dehydroxymethylation platform has been furnished. Enabled by ligand-to-metal charge transfer catalysis, an alcohol functionality has been reliably transferred into nucleophilic radicals with the loss of one molecule of formaldehyde. Intriguingly, we found that the dehydroxymethylation process can be significantly promoted by the cerium catalyst, and the stabilization effect of the fragmented radicals also plays a significant role. This operationally simple protocol has enabled the direct utilization of primary alcohols as unconventional alkyl nucleophiles for radical-mediated 1,4-conjugate additions with Michael acceptors. A broad range of alcohols, from simple ethanol to complex nucleosides and steroids, have been successfully applied to this fragment coupling transformation. Furthermore, the modularity of this catalytic system has been demonstrated in diversified radical-mediated transformations including hydrogenation, amination, alkenylation, and oxidation.
- Zhang, Kaining,Chang, Liang,An, Qing,Wang, Xin,Zuo, Zhiwei
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supporting information
p. 10556 - 10564
(2019/08/20)
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- Dehydroxymethylation of Alcohols Enabled by Cerium Photocatalysis
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Dehydroxymethylation, the direct conversion of alcohol feedstocks as alkyl synthons containing one less carbon atom, is an unconventional and underexplored strategy to exploit the ubiquity and robustness of alcohol materials. Under mild and redox-neutral reaction conditions, utilizing inexpensive cerium catalyst, the photocatalytic dehydroxymethylation platform has been furnished. Enabled by ligand-to-metal charge transfer catalysis, an alcohol functionality has been reliably transferred into nucleophilic radicals with the loss of one molecule of formaldehyde. Intriguingly, we found that the dehydroxymethylation process can be significantly promoted by the cerium catalyst, and the stabilization effect of the fragmented radicals also plays a significant role. This operationally simple protocol has enabled the direct utilization of primary alcohols as unconventional alkyl nucleophiles for radical-mediated 1,4-conjugate additions with Michael acceptors. A broad range of alcohols, from simple ethanol to complex nucleosides and steroids, have been successfully applied to this fragment coupling transformation. Furthermore, the modularity of this catalytic system has been demonstrated in diversified radical-mediated transformations including hydrogenation, amination, alkenylation, and oxidation.
- Zhang, Kaining,Chang, Liang,An, Qing,Wang, Xin,Zuo, Zhiwei
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supporting information
p. 10556 - 10564
(2019/08/28)
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- Computational and experimental studies on copper-mediated selective cascade C-H/N-H annulation of electron-deficient acrylamide with arynes
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An efficient and convenient copper-mediated method has been developed to achieve direct cascade C-H/N-H annulation to synthesize 2-quinolinones from electron-deficient acrylamides and arynes. This method highlights an emerging but simple strategy to transform inert C-H bonds into versatile functional groups in organic synthesis to provide a new method of synthesizing 2-quinolinones efficiently. Mechanistic investigations by experimental and density functional theory (DFT) studies suggest that an organometallic C-H activation via a Cu(iii) intermediate is likely to be involved in the reaction.
- Chen, Chao,Hao, Yu,Zhang, Ting-Yu,Pan, Jin-Long,Ding, Jun,Xiang, Heng-Ye,Wang, Man,Ding, Tong-Mei,Duan, Abing,Zhang, Shu-Yu
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supporting information
p. 755 - 758
(2019/01/21)
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- Gem-Dialkyl Effect in Diphosphine Ligands: Synthesis, Coordination Behavior, and Application in Pd-Catalyzed Hydroformylation
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A series of palladium complexes with C3-bridged bidentate bis(diphenylphosphino)propane ligands with substituents of varying steric bulk at the central carbon have been synthesized. The size of the gem-dialkyl substituents affects the C-C-C bond angles within the ligands and consequently the P-M-P ligand bite angles. A combination of solid-state X-ray diffraction (XRD) and density functional theory (DFT) studies has shown that an increase in substituent size results in a distortion of the 6-membered metal-ligand chair conformation toward a boat conformation, to avoid bond angle strain. The influence of the gem-dialkyl effect on the catalytic performance of the complexes in palladium-catalyzed hydroformylation of 1-octene has been investigated. While hydroformylation activity to nonanal decreases with increasing size of the gem-dialkyl substituents, a change in chemoselectivity toward nonanol via reductive hydroformylation is observed.
- Aitipamula, Srinivasulu,Britovsek, George J. P.,Nobbs, James D.,Romain, Charles,Tay, Dillon W. P.,Van Meurs, Martin,White, Andrew J. P.
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p. 663 - 671
(2020/01/02)
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- NMDA RECEPTOR MODULATORS AND USES THEREOF
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Disclosed herein, in part, are heteroaromatic compounds and methods of use in treating neuropsychiatric disorders, e.g., schizophrenia and major depressive disorder. Pharmaceutical compositions and methods of making heteroaromatic compounds are provided. The compounds are contemplated to modulate the NMDA receptor.
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Paragraph 00295
(2018/07/29)
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- Mononuclear ruthenium complex and organic synthesis reaction using same
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A neutral or cationic mononuclear ruthenium divalent complex represented by formula (1) can actualize exceptional catalytic activity in at least one reaction among a hydrosilylation reaction, hydrogenation reaction, and carbonyl compound reduction reaction. (In the formula, R1-R6 each independently represent a hydrogen atom or an alkyl group, aryl group, aralkyl group, organooxy group, monoorganoamino group, diorganoamino group, monoorganophosphino group, diorganophosphino group, monoorganosilyl group, diorganosilyl group, triorganosilyl group, or organothio group optionally substituted by X; at least one pair comprising any of R1-R3 and any of R4-R6 together represents a crosslinkable substituent; X represents a halogen atom, organooxy group, monoorganoamino group, diorganoamino group, or organothio group; L each independently represent a two-electron ligand other than CO and thiourea ligands; two L may bond to each other; and m represents an integer of 3 or 4.)
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Page/Page column 44; 46
(2018/03/26)
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- Disilaruthena- and Ferracyclic Complexes Containing Isocyanide Ligands as Effective Catalysts for Hydrogenation of Unfunctionalized Sterically Hindered Alkenes
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Disilaferra- and disilaruthenacyclic complexes containing mesityl isocyanide as a ligand, 3′ and 4′, were synthesized and characterized by spectroscopy and crystallography. Both 3′ and 4′ showed excellent catalytic activity for the hydrogenation of alkenes. Compared with iron and ruthenium carbonyl analogues, 1′ and 2′, the isocyanide complexes 3′ and 4′ were more robust under the hydrogenation conditions, and were still active even at higher temperatures (~80 °C) under high hydrogen pressure (~20 atm). The iron complex 3′ exhibited the highest catalytic activity toward hydrogenation of mono-, di-, tri-, and tetrasubstituted alkenes among currently reported iron catalysts. Ruthenium complex 4′ catalyzed hydrogenation under very mild conditions, such as room temperature and 1 atm of H2. The remarkably high catalytic activity of 4′ for hydrogenation of unfunctionalized tetrasubstituted alkenes was especially notable, because it was comparable to the activity of iridium complexes reported by Crabtree and Pfaltz, which are catalysts with the highest activity in the literature. DFT calculations suggested two plausible catalytic cycles, both of which involved activation of H2 assisted by the metal-silicon bond through σ-bond metathesis of late transition metals (oxidative hydrogen migration). The linear structure of M C≡N - C (ipso carbon of the mesityl group) played an essential role in the efficient hydrogenation of sterically hindered tetrasubstituted alkenes.
- Sunada, Yusuke,Ogushi, Hajime,Yamamoto, Taiji,Uto, Shoko,Sawano, Mina,Tahara, Atsushi,Tanaka, Hiromasa,Shiota, Yoshihito,Yoshizawa, Kazunari,Nagashima, Hideo
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supporting information
p. 4119 - 4134
(2018/03/29)
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- A amide alkaloid fully synthetic method
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The invention discloses a total synthesis method of amides alkaloid, and belongs to the technical field of the chemistry of natural products. The total synthesis method comprises the following steps: carrying out the synthesis by adopting malonate and 2-bromopropane or 2-bromopropane derivative as raw materials, thereby obtaining isopropyl malonate; (2) carrying out the synthesis by adopting 2-aminopyrrolidine as a raw material, thereby obtaining mid-body 2-amino tetralin pyrrolidine; and (3) synthesizing amides alkaloid 3-isopropyl-nafoxidine[1,2-alpha]pyrimidine-2,4(1H,3H)-diketone and a derivative by adopting the isopropyl malonate and the 2-2-amino tetralin pyrrolidine as a raw material. By adopting the total synthesis method, the defect that the extraction separation process in the natural product is complicated and the yield is low can be overcome, and the demand of perople for further researching the natural product can be satisfied; moreover, the synthesis method is simple in route, raw materials are cheap and easy to obtain, and the yield is relatively high.
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Paragraph 0039; 0040; 0041; 0042
(2017/08/25)
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- Bifunctional Iminophosphorane Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α-Substituted Acrylate Esters
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The highly enantioselective sulfa-Michael addition of alkyl thiols to unactivated α-substituted acrylate esters catalyzed by a bifunctional iminophosphorane organocatalyst under mild conditions is described. The strong Br?nsted basicity of the iminophosphorane moiety of the catalyst provides the necessary activation of the alkyl thiol pro-nucleophile, while the two tert-leucine residues flanking a central thiourea hydrogen-bond donor facilitate high enantiofacial selectivity in the protonation of the transient enolate intermediate. The reaction is broad in scope with respect to the alkyl thiol, the ester moiety, and the α-substituent of the α,β-unsaturated ester, affords sulfa-Michael adducts in excellent yields (up to >99%) and enantioselectivities (up to 96% ee), and is amenable to decagram scale-up using catalyst loadings as low as 0.05 mol %.
- Farley, Alistair J. M.,Sandford, Christopher,Dixon, Darren J.
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supporting information
p. 15992 - 15995
(2016/01/15)
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- PROCESSES FOR PREPARING HIV REVERSE TRANSCRIPTASE INHIBITORS
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Compounds of Formula (I): can be prepared by a multi-step process from compounds of Formula (II): wherein G is Cl, Br or I.
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Page/Page column 13-14
(2009/07/10)
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- Pheromones and analogs from Neozeleboria wasps and the orchids that seduce them: a versatile synthesis of 2,5-dialkylated 1,3-cyclohexanediones
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Chiloglottone, a wasp pheromone and attractant of sexually deceptive Chiloglottis orchids, and several structural analogs were synthesized. The synthetic approach is facile, high yielding and versatile, enabling rapid divergence to generate dialkylated analogs of chiloglottone. The key transformation was an organocadmium-mediated desymmetrization of glutaric anhydride derivatives. This library of synthetic 2,5-dialkylated 1,3-cyclohexanediones may assist in future identification of natural products in further species.
- Poldy, Jacqueline,Peakall, Rod,Barrow, Russell A.
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p. 2446 - 2449
(2008/09/20)
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- Total Synthesis of (±)-Isocembrene: A Tactic for both Diene Construction and Macrocycle Formation
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The total synthesis of (±)-isocembrene 1, a naturally occurring cembrene diterpenoid, has been achieved via a unified, convergent and highly efficient strategy by imploying an intramolecular Stille sp2-sp 2 macrocyclization as the key step and it presents an ideal opportunity to extend the effectiveness of the tactic for both 1,3-diene construction and macrocycle formation.
- Zhang, Fengzhi,Peng, Lizeng,Zhang, Tao,Mei, Tiansheng,Liu, Huawei,Li, Yulin
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p. 3761 - 3770
(2007/10/03)
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- Alkylation of malonic and acetoacetic esters in an ionic liquid
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1-Butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6]) has been used as a recyclable medium in the alkylation of malonic and acetoacetic esters with alkyl, benzyl and prenyl halides.
- Kryshtal, Galina V.,Zhdankina, Galina M.,Zlotin, Sergei G.
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- Mixed Dialkylaluminum Chlorides and Mixed Trimethylorganoaluminates in Chemoselective 1,4 Addition Reactions to Alkylidene Malonic Acid Diethyl Ester
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Mixed alkyl-methyl- and aryl-methylorganoaluminum chlorides 6 were formed by reaction of methylaluminum dichloride with organolithium or Grignard compounds and used for chemoselective 1,4 addition of higher alkyl, aryl, alkenyl and alkinyl groups to alkylidine malonic esters 1 and 2. As an alternative, mixed trimethylorganoaluminates 7 can also be applied for these Michael addition reactions. For conjugate addition of alkenyl groups to alkylidene malonates 1 and 2, alkenyl diisopropylalanes 10 obtained from alkynes and diisopropylaluminum hydride proved the most efficient reagents. Using these novel mixed organoaluminum compounds, β-branched malonic (carboxylic) acid derivatives 3c, 8, 9 and 11 were obtained in good yields. The method offers a general access to β-branched carboxylic derivatives of quite diverse structure not dependent on the commercial availability of the organoluminum chlorides.
- Maas, Steffen,Kunz, Horst
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p. 396 - 403
(2007/10/03)
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- Conjugate addition of dialkylaluminum chlorides to alkylidenemalonic acid derivatives
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Complete regioselectivity is achieved in conjugate addition reactions of dialkylaluminum chlorides with alkylidenemalonic esters, alkylidenecyanoacetates, and alkylidenemalonodinitrile to give β-branched carboxylic acid derivatives. Sterically demanding products containing quaternary carbon atoms are obtained in good yields. In the case of diethylaluminum chloride, accompanying reductions of the substrates can be suppressed by application of boron trifluoride as an assisting Lewis acid.
- Maas, Steffen,Stamm, Armin,Kunz, Horst
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p. 1792 - 1798
(2007/10/03)
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- Use of the Nonionic Superbase P(MeNCH2CH2)3N in the Selective Monoalkylation of Active-Methylene Compounds
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The symmetric active-methylene compounds CH2(CO2Et)2 and CH2[C(O)Me]2 are selectively monoalkylated in the presence of 1.1 equiv of a variety of alkyl halides and 1 equiv of the nonionic Superbase P(MeNCH2CH2)2N in 85-98% yields in 30 min at room temperature. The unsymmetrical active-methylene compound EtO2CCH2C(O)Me is selectively monoalkylated under the same conditions, except for the temperature, which is 0 °C, in 59-88% yields. The observation of selective C- rather than O-alkylation is rationalized in terms of the formation of an enolate whose negatively charged oxygen is sterically protected by a nearby HP(MeNCH2CH2)2N+ counterion in a tight ion pair.
- Arumugam, Subramaniam,McLeod, Dale,Verkade, John G.
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p. 3677 - 3679
(2007/10/03)
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- Nitration of α,β-unsaturated esters. Evidence for positive charge build-up adjacent to carbonyl carbon
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Reactive intermediates formed in the nitration of certain α,β-unsaturated esters with nitronium tetrafluoroborate exhibit behaviour expected of highly reactive α-carbonyl cations. Three diagnostic reaction types have been observed which indicate the presence of these destabilised cations: (i) trapping in a Ritter reaction, (ii) cyclopropane formation from propyl cations, (iii) Wagner-Meerwein migration of alkyl groups. Semi-empirical calculations of the relative gas-phase stabilities of the proposed intermediate cations are useful in rationalising the observed chemistry.
- Hewlins, Stuart A.,Murphy, John A.,Lin, Jian,Hibbs, David E.,Hursthouse, Michael B.
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p. 1559 - 1570
(2007/10/03)
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- Reduction of Diethyl Alkylidenemalonates and Ethyl Propylideneacetoacetate with Complex Metal Hydrides
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Reduction of diethyl alkylidenemalonates and ethyl propylideneacetoacetate with complex metal hydrides occurs at the olefinic moiety. The reduction with NaBH4 in t-BuOH-MeOH yields saturated 1,3-diols; LiAlH4 as reducing agent gives rise to corresponding saturated esters. With NaAlH4 in THF, a mixture of products is formed, which contains considerable amounts of the initial ester and low-boiling compounds; ethyl propylideneacetoacetate is also reduced to ethyl propylacetoacetate. The system NaBH4-AlBr3 in THF almost does not reduce diethyl isopropylidenemalonate, whereas under the same conditions ethyl propylideneacetoacetate is converted into ethyl 2-(1-hydroxyethyl)pentanoate.
- Kuznetsov,Alekseeva,Gren'
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p. 396 - 399
(2007/10/03)
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- 1,1,1-TRICHLORO-3--3,4-EPOXYBUTANE
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The synthesis of 1,1,1-trichloro-3--3,4-epoxybutane has been accomplished in nine steps from diethyl malonate and urea.The epoxide was prepared from the olefinic precursor via oxidation with anhydrous trifluoroperacetic acid in a non-buffered system.Product isolation from trifluoroacetic acid solution demonstrates an unexpected stability of this class of epoxides toward protonic media.
- Pews, R. Garth,Puckett, Wallace E.
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p. 179 - 186
(2007/10/02)
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- ORGANOMANGANESE (II) REAGENTS XV. CONJUGATE ADDITION OF ORGANOMANGANESE REAGENTS TO ALKYLIDENEMALONIC ESTERS AND RELATED COMPOUNDS
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Organomanganese reagents react with alkylidenemalonic esters or related compounds to give the conjugate addition products in good yields.Several examples illustrate the scope and the efficiency of this reaction.
- Cahiez, Gerard,Alami, Mouad
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p. 4163 - 4176
(2007/10/02)
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- SELECTIVE REDUCTION OF CONJUGATED ETHYLENIC LINKAGE IN THE PRESENCE OF ION-EXCHANGE RESIN BOUND BOROHYDRIDE.
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The use of crosslinked polystyrene anion-exchange resin as a support for borohydride ions made it possible to reduce conjugated olefinic bonds selectively under very mild conditions.The isolation of the reduced products by a simple filtration and evaporation process is another interesting feature of this reaction.
- Nag, Ahindra,Sarkar, Ashis,Sarkar, Samir K.,Palit, Sunanda K.
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p. 1007 - 1014
(2007/10/02)
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- Alpha-cyano-phenoxybenzyl-isovalerates
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Compounds of the formula STR1 wherein R is alkenyl, aralkyl or alkyl; X is H, CN, thioamide, or alkynyl; and Y is phenoxyphenyl or phthalimido, are useful as pesticides.
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