153184-13-5Relevant academic research and scientific papers
Photoinduced Copper-Catalyzed Asymmetric Decarboxylative Alkynylation with Terminal Alkynes
Dong, Xiao-Yang,Du, Xuan-Yi,Fang, Jia-Heng,Gu, Qiang-Shuai,Li, Zhong-Liang,Liu, Xin-Yuan,Wang, Li-Lei,Xia, Hai-Dong
supporting information, p. 16926 - 16932 (2020/08/25)
We describe a photoinduced copper-catalyzed asymmetric radical decarboxylative alkynylation of bench-stable N-hydroxyphthalimide(NHP)-type esters of racemic alkyl carboxylic acids with terminal alkynes, which provides a flexible platform for the construction of chiral C(sp3)?C(sp) bonds. Critical to the success of this process are not only the use of the copper catalyst as a dual photo- and cross-coupling catalyst but also tuning of the NHP-type esters to inhibit the facile homodimerization of the alkyl radical and terminal alkyne, respectively. Owing to the use of stable and easily available NHP-type esters, the reaction features a broader substrate scope compared with reactions using the alkyl halide counterparts, covering (hetero)benzyl-, allyl-, and aminocarbonyl-substituted carboxylic acid derivatives, and (hetero)aryl and alkyl as well as silyl alkynes, thus providing a vital complementary approach to the previously reported method.
Concise Synthesis of 2-Arylpropanoic Acids and Study of Unprecedented Reduction of 3-Hydroxy-2-arylpropenoic Acid Ethyl Ester to 2-Arylpropenoic Acid Ethyl Ester by BH3·THF
Shahid Islam,Ahmad, Syarhabil,Attu, Mary Rose,Foerstering, F. Holger,Mahmun Hossain
, p. 1273 - 1286 (2015/09/22)
We have developed a concise method of synthesizing racemic arylpropanoic acids, which have been widely used as nonsteroidal anti-inflammatory drugs (NSAIDs). The synthesis involves only four steps from commercially available benzaldehyde. The synthesis incorporates an unprecedented reduction reaction, conversion of 3-hydroxy-2-arylpropenoic acid ethyl ester to 2-arylpropenoic acid ethyl ester by BH3·THF. The reduction reaction has been investigated and optimized.
NOVEL CONDENSED-RING PYRROLIDINE DERIVATIVE
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Paragraph 0193-0195, (2018/11/22)
PROBLEM TO BE SOLVED: To provide a condensed-ring pyrrolidine derivative that selectively activates muscarine M1 and M4 receptors to express the effect and has reduced side effects via other muscarine receptors or other receptors. SO
Synthesis of N-alkoxyindol-2-ones by copper-catalyzed intramolecular N-arylation of hydroxamates
Kukosha, Tatyana,Trufilkina, Nadezhda,Katkevics, Martins
, p. 2525 - 2528 (2011/11/13)
The first example of copper-catalyzed intramolecular N-arylation of hydroxamic acid derivatives is presented. Based on this transformation a new method for the synthesis of N-alkoxyindol-2-ones from 2-(2-bromoaryl) acetylhydroxamates has been developed. T
Aryl-oxazoline chelates of first-row transition metals: Structures of {Κ-C,N-(o-C6H4)CMe2(COCH 2CMe2N)}FeCl(py) and [(Κ-C,N-(o-C6H 4)CMe2(COCH2CMe2N)}Cr(μ-Cl)] 2
Volpe, Emily C.,Manke, David R.,Bartholomew, Erika R.,Wolczanski, Peter T.,Lobkovsky, Emil B.
scheme or table, p. 6642 - 6652 (2011/02/27)
Aryl-oxazoline synthons have been explored for the preparation of strong-field first-row transition metal chelate species. With 4,4-dimethyl-2-phenyloxazoline (HPhOx), no CH bond activations afforded complexation, and aside from Zn(Κ-C,N-4,4-Me2-2-(o-C 6H4)oxazoline)2 (Zn(PhOx)2), aryl-coupling reactions were noted with 4,4-dimethyl-2-(2-lithiophenyl)oxazoline (LiPhOx) and MX2; [Κ-N,N-{4,4-Me2-(2-o-C 6H4)-2-oxazoline}2]CoCl2 (1-Co) was structurally characterized. Metalations with 4,4-dimethyl-2-benzyloxazoline (PhCH2Ox) were prone to deprotonation, as exemplified by (Me 2N)3Ti(η-N-(4,4-dimethyl-(2-CHPh)oxazoline)) (2) and bis-N,N′-(4,4-dimethyl-(2-pyridylmethylyl)oxazoline)Fe (3). Oxidative addition of 4,4-dimethyl-2-(2-bromophenylpropan-2-yl)oxazoline (BrPhCMe 2Ox) to Ni(COD)2 provided [{Κ-C,N-(o-C 6H4)CMe2(COCH2CMe 2N)}Ni]2(μ-Br)2 (42). With 4,4-dimethyl-2-(2-lithiophenylpropan-2-yl)oxazoline (LiPhCMe2Ox), salt (FeBr2) metathesis proved uncompetitive with oxazoline ring-opening, as exhibited by [{Κ-N,O-C6H4CMe 2C=NCMe2CH2(μ-O)-}BrFe{Κ-N,O-C 6H4CMe2C=NCMe2CH2(μ-O) -}FeBr]Li {Κ-N,O-C6H4CMe2-C=NCMe 2CH2(μ-O)-}(DME) (5-Fe2Li). Metatheses utilizing (PhCMe2Ox)2Zn, prepared from LiPhCMe 2Ox and ZnCl2, gave structurally characterized dichromium, i.e., [{Κ-C,N-(o-C6H4)CMe2 (COCH 2CMe2N)}Cr]2(μ-Cl)2 (6 2), and iron, i.e., {Κ-C,N-{(o-C6H 4)CMe2(COCH2CMe2N)}Fe(py)Cl (7) products. Bis-aryloxazoline metal complexes proved difficult to prepare, with {Κ-C,N-(o-C6H4)CMe2(COCH 2CMe2N)}2M (M = Ni, 9) the only clear example, although NMR evidence exists for M = Fe (8).
Synthesis and potent anticonvulsant activities of 4-oxo-imidazo[1,2-a]indeno[1,2-e]pyrazin-8- and -9-carboxylic (acetic) acid AMPA antagonists
Pratt, Jeremy,Jimonet, Patrick,Bohme, Georg Andrees,Boireau, Alain,Damour, Dominique,Debono, Marc Williams,Genevois-Borella, Arielle,Randle, John C.R,Ribeill, Yves,Stutzmann, Jean-Marie,Vuilhorgne, Marc,Mignani, Serge
, p. 2749 - 2754 (2007/10/03)
The over-stimulation of excitatory amino acid receptors such as the glutamate AMPA receptor has been suggested to be associated with neurodegenerative disorders. Here we describe an original series of readily water soluble 4-oxo-imidazo[1,2-a] indeno[1,2-
5H, 10H-IMIDAZO[1,2-A]INDENO[1,2-E] PYRAZIN-4-ONE DERIVATIVES, PREPARATION THEREOF, AND DRUGS CONTAINING SAID DERIVATIVES
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, (2008/06/13)
Compounds of formula (I), wherein R is a hydrogen atom or a carboxy, alkoxycarbonyl,--CO--NR 4 R 5,--PO 3 H 2 or--CH 2 OH radical, and R 1 is an-alk-NH 2,-alk-NH--CO--R 3,-alk-COOR 4,-alk-CO--NR 5 R 6 or--CO--NH--R 7 radical. The compounds of formula (I) have valuable pharmacological properties and are antagonists of the α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor also known as the quisqualate receptor. Furthermore, the compounds of formula (I) are non-competitive antagonists of the N-methyl-D-aspartame (NMDA) receptor and more specifically are ligands for NMDA receptor glycine modulator sites.
Presynaptic cholinergic modulators as potent cognition enhancers and analgesic drugs. 1. Tropic and 2-phenylpropionic acid esters
Gualtieri,Conti,Dei,Giovannoni,Nannucci,Romanelli,Scapecchi,Teodori,Fanfani,Ghelardini,Giotti,Bartolini
, p. 1704 - 1711 (2007/10/02)
Previous studies have shown that (R)-(+)-hyoscyamine has analgesic activity as a consequence of increased ACh release following antagonism of central muscarinic autoreceptors. Since the enhancement of central cholinergic transmission could be beneficial for cognitive disorders, we manipulated (R)-(+)-hyoscyamine, synthesizing several derivatives of tropic and 2-phenylpropionic acids, with the aim of obtaining drugs which are able to increase ACh release and consequently to show analgesic and nootropic activities. The results showed that several new compounds are indeed potent analgesics (with an analgesic efficacy comparable to that of morphine) and that the most potent one ((±)-19, PG9) also has remarkable cognition- enhancing properties. Our study confirmed that the mechanism of action involves ACh release even if it is still unclear whether only muscarinic autoreceptors or, also, heteroreceptors are involved.
Directed lithiations: The effect of varying directing group orientation on competitive efficiencies for a series of tertiary amide, secondary amide, and alkoxide directed ortho lithiations
Beak, Peter,Kerrick, Shawn T.,Gallagher, Donald J.
, p. 10628 - 10636 (2007/10/02)
Significant differences for competitive efficiencies in directed ortho lithiations for single functional groups in three series, the secondary benzamides 1-4, the tertiary benzamides 5-11, and the benzylic alcohols 12-17, are reported. For both amide seri
