- Transition-metal-free decarboxylation of dimethyl malonate: An efficient construction of α-amino acid esters using TBAI/TBHP
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A transition-metal-free decarboxylation coupling process for the preparation of α-amino acid esters, which succeeded in merging hydrolysis/decarboxylation/nucleophilic substitution, is well described. This strategy uses commercially available inexpensive starting materials, catalysts and oxidants and has a wide substrate scope and operational simplicity. This journal is
- Zhang, Jie,Shao, Ying,Wang, Yaxiong,Li, Huihuang,Xu, Dongmei,Wan, Xiaobing
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p. 3982 - 3987
(2015/03/30)
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- Iodine-mediated one-pot synthesis of indoles and 3-dimethylaminoindoles via annulation of enaminones
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The synthesis of 2-carbonylindoles was achieved via a iodine-mediated cyclization of the corresponding enaminone precursors, which were formed by reaction of the ?-arylaminomethylene carbonyl derivatives with N,N'-dimethylformamide dimethyl acetal (DMFDMA). An alternative and more efficient procedure consisted of a similar cyclization of the enaminones, but under solvent-free and grinding reaction conditions. In another iodine-promoted procedure, 2-carbonyl-3-dimethylaminoindoles were synthesized via a one-pot cascade reaction between the α-arylaminomethylene carbonyl derivative and DMFDMA.ARKAT-USA, Inc.
- Jerezano, Alberto V.,Labarrios, Ehecatl M.,Jimenez, Fabiola E.,Del Cruz, Maria Carmen,Pazos, Diana C.,Gutierrez, Rsuini U.,Delgado, Francisco,Tamariz, Joaquin
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- A new strategy for the construction of α-amino acid esters via decarboxylation
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A new α-amino acid esters formation reaction has been developed via decarboxylation. The methodology is distinguished by its practical novelty in terms of the readily accessible starting materials, environmentally benign reaction conditions and waste streams, and wide substrate scope.
- Zhang, Jie,Jiang, Jiewen,Li, Yuling,Zhao, Yun,Wan, Xiaobing
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supporting information
p. 3222 - 3225
(2013/07/26)
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- Synthesis and biological evaluation of 1,4-diazepane derivatives as T-type calcium channel blockers
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We have synthesized and biologically evaluated 1,4-diazepane derivatives as T-type calcium channel blockers. In this study, we discovered compound 4s, a potential T-type calcium channel blocker with good selectivity over hERG and N-type calcium channels. In addition, it exhibited favorable pharmacokinetic characteristics for further investigation of T-type calcium channel related diseases.
- Gu, Su Jin,Lee, Jae Kyun,Pae, Ae Nim,Chung, Hye Jin,Rhim, Hyewon,Han, So Yeob,Min, Sun-Joon,Cho, Yong Seo
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scheme or table
p. 2705 - 2708
(2010/07/15)
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- Copper-catalyzed enantioselective propargylic amination of propargylic esters with amines: Copper-allenylidene complexes as key intermediates
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The scope and limitations of the copper-catalyzed propargylic amination of various propargylic esters with amines are presented, where optically active diphosphines such as Cl-MeO-BIPHEP and BINAP work as good chiral ligands. A variety of secondary amines are available as nucleophiles for this catalytic reaction to give the corresponding propargylic amines with a high enantioselectivity. The results of some stoichiometric and catalytic reactions indicate that the catalytic amination proceeds via copper-allenylidene complexes formed in situ, where the attack of amines to the electrophilic γ-carbon atom in the allenylidene complex is an important step for the stereoselection. Investigation of the relative rate constants for the reaction of several para-substituted propargylic acetates with N-methylanilines reveals that the formation of the copper-allenylidene complexes is involved in the rate-determining step. The result of the density functional theory calculation on a model reaction also supports the proposed reaction pathway involving copper-allenylidene complexes as key intermediates. The catalytic procedure presented here provides a versatile and direct method for the preparation of a variety of chiral propargylic amines.
- Hattori, Gaku,Sakata, Ken,Matsuzawa, Hiroshi,Tanabe, Yoshiaki,Miyake, Yoshihiro,Nishibayashi, Yoshiaki
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supporting information; experimental part
p. 10592 - 10608
(2010/09/10)
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- Practical syntheses of oxindole derivatives: Chemical development towards 2-(5-chloro-2-oxo-2,3-dihydroindol-1-yl)acetamide and (S)-2-(5-Chloro-2-oxo-2,3- dihydroindol-1-yl)propionamide
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We describe development of scalable syntheses of novel oxindole-type SV2A ligands with improved potency towards seizure suppression.
- Broeders, Fabienne,Defrere, Laurent,Deltent, Marie-France,Driessens, Frank,Gilson, Frederic,Grooters, Luc,Ikonomakos, Xavier,Limauge, Frederic,Sergeef, Emmanuel,Verstraeten, Natacha
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experimental part
p. 442 - 449
(2010/04/22)
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- Regioselective and versatile synthesis of indoles via intramolecular Friedel-Crafts heteroannulation of enaminones
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A new approach is described for the synthesis of substituted indoles 5, through an intramolecular and regioselective Friedel-Crafts cyclization of enaminones 6a-h catalyzed by Lewis acids. Compounds 6 were prepared from the 2-anilinocarbonyl compounds 7, by treatment with DMFDMA under thermal or microwave (MW) irradiation conditions. An alternative and shorter one-pot two-step synthesis of indoles 5 was achieved starting from compounds 7 and promoted by MW radiation, including the elusive 2-acetylindoles 5i-m. Georg Thieme Verlag Stuttgart.
- Cruz, María Del Carmen,Jiménez, Fabiola,Delgado, Francisco,Tamariz, Joaquín
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p. 749 - 755
(2007/10/03)
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- Soluble Polymer-Supported Synthesis of α-Amino Acid Derivatives
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A practical and efficient synthesis of N-substituted α-amino acid derivatives on soluble polymer support is described.
- Hu, Chunling,Chen, Zuxing,Yang, Guichun
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p. 219 - 224
(2007/10/03)
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- CHEMICAL COMPOUNDS
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Triazine derivatives of formula (I) or salts thereof, wherein R1 represents a halogen atom or a group selected from hydroxy; C1-8 alkyl C1-6 alkoxy; C1-3 alkoxy C1-3 alkoxy; phenoxy or phenyl C1-3 alkoxy, wherein the phenyl group is optionally substituted by a halogen atom or a group selected from C1-3 alkyl, C1.3 alkoxy, or hydroxy; fluoro C1-3 alkyl; cyano; -CO2R3, wherein R3 represents a hydrogen atom or a C1-4 alkyl group; - CONR4R5, wherein R4 and R5 each independently represents a hydrogen atom or a C1-4 alkyl group, or, together with the nitrogen atom to which they are attached, form a saturated 5- to 7- membered ring, which ring optionally contains one or more atoms selected from an oxygen or a sulphur atom, or a group selected from -NH- or -N(CH3)-; and R2 represents a hydrogen or halogen atom, or a group selected from hydroxy, C1-6 alkyl or C1-6 alkoxy; are inhibitors of the enzyme 5-lipoxygenase. Processes for preparing the triazine derivatives of formula (I) and compositions containing them are also described
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- Production of an ester of one enantiomer of an α-amino acid in the form of a salt with an optically active acid
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A process for the production of an ester of one enantiomer of an α-amino acid in the form of a salt with an optically active acid, which comprises reacting an ester of the opposite enantiomer of said α-amino acid (which may be in admixture with an ester of the desired enantiomer) with said optically active acid and an aldehyde or ketone, whereby an ester of the desired enantiomer separates out in the form of the said salt. The free α-amino acid and/or its salts may be obtained by hydrolysis of the ester thus formed. Optically active α-amino acids and their esters are of use in the synthesis of physiologically active compounds e.g. antibiotics of the penicillin and cephalosporin types. The present invention provides a relatively cheap, high yield process for the production of esters of optically active α-amino acids and for the production of optically active α-amino acids thereform. Certain novel compounds are disclosed.
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