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1.
Yu. A. Zhuravleva A. V. Zimichev M. N. Zemtsova Yu. N. Klimochkin 《Russian Journal of Organic Chemistry》2009,45(4):609-612
Reduction of some substituted quinoline-4-carboxylic acids was studied. The reduction of 2-alkylquinoline-4-carboxylic acids
with Raney nickel in aqueous alkali was stereoselective, and the resulting 2-alkyl-1,2,3,4-tetrahydroquinoline-4-carboxylic
acids were individual cis isomers.
Original Russian Text ? Yu.A. Zhuravleva, A.V. Zimichev, M.N. Zemtsova, Yu.N. Klimochkin, 2009, published in Zhurnal Organicheskoi
Khimii, 2009, Vol. 45, No. 4, pp. 622–625. 相似文献
2.
The condensation of 4-oxo-1,2,3,4-tetrahydroquinoline-7-carboxylic acid and its 6-chloro analog with aromatic aldehydes has given the corresponding 3-benzyl-4-oxo-1,4-dihydroquinoline-7-carboxylic acids and their 4-chloro derivatives.For Communication II, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 8, pp.1115–1118, August, 1970. 相似文献
3.
Giampiero Pagani Zecchini Mario Paglialunga Paradisi 《Journal of heterocyclic chemistry》1979,16(8):1589-1597
Treatment of protected dipeptides containing 1,2,3,4-tetrahydroquinoline-2-carboxylic acid with acetic anhydride affords only 1H,3H,5H-oxazolo[3,4-a]quinolin-3-one derivatives. The formation of a-acylaminomethylketones, arising from the competitive Dakin-West reaction, was generally observed when the cyclization procedure was extended to some amides of the cyclic imino acid. The preferential stabilization of one of two probable mesoionic intermediates seems to determine the preferred pathway. 相似文献
4.
Stanislav Kafka Michal Kov Antonín Klsek Thomas Kappe 《Journal of heterocyclic chemistry》1996,33(6):1977-1982
The Wittig reaction of 3-hydroxy-1,2,3,4-tetrahydroquinoline-2,4-diones 2 with ethyl (triphenyl-phosphoranylidene)acetate 3 proceeds stereoselectively to give E-4-carbethoxymethylene-1,2,3,4-tetra-hydro-2-quinolones 4 , which were hydrolyzed to corresponding acids 6 Butenolides 5 were detected and, in some cases, isolated as a minor product of the Wittig reaction. 相似文献
5.
A. Sobolev B. Vigante Ya. Ozols G. Duburs 《Chemistry of Heterocyclic Compounds》1996,32(10):1189-1195
Reduction of esters of 2-metylquinoline-3-carboxylic acids and their perchlorates gave esters of 1,4-dihydro-2-methylquinoline-3-carboxylates, while derivatives of 1,2-dihydroquinoline were formed in the case of 1,2-dimethyl-3-ethoxycarbonyl-7-methoxyquinolinium perchlorate. Reduction of esters of 2-methylquinoline-3-carboxylic acid, 1,2-dimethyl-3-ethoxycarbonyl-1-methoxyquinolinium perchlorate and 3-acetyl-2-methyl-quinoline with sodium tetrahydroborate in acetic acid gave esters of 1,2-dimethyl- and 2-methyl-1,2,3,4-tetrahydroquinoline-3-carboxylic acid and 3-acetyl-2-methyl-1,2,3,4-tetrahydroquinoline.Latvian Institute of Organic Synthesis, Riga, LV-1006. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1383–1390, October, 1996. Original article submitted October 11, 1995. 相似文献
6.
D. A. Rudenko S. N. Shurov M. I. Kodess M. A. Ezhikova A. N. Vasyanin 《Russian Journal of Organic Chemistry》2012,48(6):799-803
2-Substituted 7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-4-carboxylic acids were synthesized by reaction of acyl- and aroylpyruvic acids with 3-amino-5,5-dimethylcyclohex-2-en-1-one. A plausible mechanism of their formation was proposed on the basis of ab initio quantum-chemical calculations. 相似文献
7.
A. Péter G. Török G. Tóth W. Van Den Nest G. Laus D. Tourwé D. W. Armstrong 《Chromatographia》1998,48(1-2):53-58
Summary High-performance liquid chromatographic and gas chromatographic methods were developed for the separation of unusual secondary
aromatic amino acids. Amino acids containing 1,2,3,4-tetrahydroisoquinoline, 1,2,3,4-tetrahydronorharmane-1-carboxylic acid
and 1,2,3,4-tetrahydro-3-carboxy-2-carboline moieties were synthetized in racemic or chiral forms. The high-performance liquid
chromatography was carried out either on a teicoplanin-containing chiral stationary phase or on an achiral C18 column. In the latter case the diastereomers of the amino acids formed by precolumn derivatization with the chiral reagents
2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate or 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide were separated. The gas chromatographic
analyses were based on separation on a Chirasil-L-Val column.
Presented at: Balaton Symposium on High-Performance Separation Methods, Siófok, Hungary, September 3–5, 1997 相似文献
8.
The preparation of 2,3a,4,5-tetrahydrofuro[2,3-c]quinoline-2,4-diones starting from 3-hydroxy-1,2,3,4-tetrahydroquinoline-2,4-diones and using the reaction path via bromoacetylderivatives and triphenylphosphonioacetyl derivatives of the initial substances is described. The nmr spectra of the products are discussed. 相似文献
9.
A series of 4-aminomethyl-1,2,3,4-tetrahydroisoquinoline derivatives were prepared as potential CNS-agents acting via amino-acid neurotransmitter systems. The compounds were synthesized from 1,2,3,4-tetra-hydro-1-oxoisoquinoline-4-carboxylic acids obtained by dipolar cycloaddition reactions of imines with homo-phthalic anhydride. Among the compounds tested 5c and 5m showed sub-micromolar affinity for the NMDA receptor and represent a structurally novel class of ligand for this site. 相似文献
10.
Farnaz Jafarpour Nafiseh Jalalimanesh Mina Barzegar Amiri Olia Asieh Otaredi Kashani 《Tetrahedron》2010,66(49):9508-9511
A simple and highly efficient protocol with mild reaction conditions has been developed that allows the smooth protiodecarboxylation of diversely functionalized coumarin-3-carboxylic acids. In the presence of catalytic amounts of Ag2CO3 and acetic acid, even un-activated coumarin-3-carboxylic acids were converted in good to excellent yields and with great preparative ease to the corresponding coumarin derivatives. 相似文献
11.
A diastereoselective synthesis of 1-methyl-2-alkyl- and 2-alkyl-1,2,3,4-tetrahydroquinoline-4-carboxylic esters has been developed from methyl (2-nitrophenyl)acetate (1). The method involves alkylation of 1 with an allylic halide, ozonolysis of the double bond, and catalytic hydrogenation. The final hydrogenation initiates a tandem sequence involving (1) reduction of the aromatic nitro group, (2) condensation of the aniline or hydroxylamine(8) nitrogen with the side chain carbonyl, (3) reduction of the resulting nitrogen intermediate, and (4) reductive amination of the tetrahydroquinoline with formaldehyde produced in the ozonolysis to give a methyl (+/-)-1-methyl-2-alkyl-1,2,3,4-tetrahydroquinoline-4-carboxylate. Removal of the formaldehyde prior to hydrogenation gives the simple (+/-)-2-alkyl derivatives. The products are isolated in high yield as single diastereomers having the C-2 alkyl group cis to the C-4 carboxylic ester. The reaction has been extended to the synthesis of tricyclic structures with similar high diastereoselection. 相似文献
12.
Reaction of N-benzoyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid with acetic anhydride resulted in 1H,3H,5H-oxazolo[3,4-a]quinolin-3-one derivative 13. Different cyclopropanation processes were applied to 13, but only diazomethane in the presence of water furnished the hitherto unknown methyl 1,2,7,7a-tetrahydro-1aH-cyclopropa[b]quinoline-1a-carboxylate 14, which can be considered as a doubly constrained 1-aminocyclopropane-1-carboxylic acid system. The mechanism of the cyclopropanation was studied in detail. The new ACC ester 14 was transformed into fused tetracyclic hydantoin derivatives, which comprised a new type of heterocyclic system. 相似文献
13.
M. G. Abramyants D. A. Lomov T. I. Zavyazkina 《Russian Journal of Organic Chemistry》2016,52(11):1610-1615
Oxidative dehydrogenation of 1-aryl(hetaryl)-1,2,3,4-tetrahydro-9Н-β-carboline-3-carboxylic acids derivatives with dimethyl sulfoxide leads to the formation of 1-aryl(hetaryl)-9Н-β-carbolines. Simultaneously with the dehydrogenation decarboxylation occurs. At the oxidation with dimethyl sulfoxide of methyl 1-aryl (hetaryl)-1,2,3,4-tetrahydro-9Н-β-carboline-3-carboxylicates methyl 1-aryl(hetaryl)-9Н-β-carboline-3-carboxylates formed whose hydrolysis afforded the corresponding 1-aryl(hetaryl)-9Н-β-carboline-3-carboxylic acids. 相似文献
14.
AbstractTwo reaction systems have been developed for the decarboxylation of indole-3-carboxylic acids. The decarboxylation can be achieved smoothly under K2CO3-catalyzed or acetonitrile-promoted basic conditions. It provided an efficient and simple method for the transformation of indole-3-carboxylic acids and the corresponding indoles were isolated with good to excellent yields. From the experimental facts, we put forward the possible reaction mechanism. 相似文献
15.
Alan Barcon Andrew P. J. Brunskill Roger A. Lalancette Hugh W. Thompson Allan J. Miller 《Acta Crystallographica. Section C, Structural Chemistry》2001,57(3):325-328
The crystal structure of (±)-4-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (C11H10O3) involves projection of the carboxyl group nearly orthogonal to the aromatic plane and hydrogen bonding of the acid groups by centrosymmetric pairing across the a edge and the center of the chosen cell [O⃛O = 2.705 (2) Å]. Intermolecular C—H⃛O=C close contacts to translationally related molecules are found for both the ketone (2.55 Å) and the acid (2.67 Å). In (±)-1-oxo-1,2,3,4-tetrahydronaphthalene-2-acetic acid (C12H12O3), the aggregation involves centrosymmetric carboxyl dimers mutually hydrogen bonded across the bc face and the a edge of the chosen cell [O⃛O = 2.674 (2) Å]. A 2.60 Å close C—H⃛O=C contact is found to the carboxyl group of centrosymmetrically related molecule. 相似文献
16.
Arylamides of 8-benzylidene-2-methyl-5,6,7,8-tetrahydroquinoline-3-carboxylic acid were obtained by treating the ethyl ester with dimagnesylamines. An example is given of their conversion to 8-benzylidene-2-styryl-5,6,7,8-tetrahydroquinoline-3-carboxylic acid anilides and subsequent cyclization to 1-oxo-1,2,3,4,6,7,8,9-octa-hydrobenzo[b]-1,6-naphthyridines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 506–508. April, 1986. 相似文献
17.
B. Shtrumfs D. Chernyak I. Kums I. Kalvins P. Trapencieris 《Chemistry of Heterocyclic Compounds》2004,40(6):725-733
A series of N-unsubstituted esters of aziridine-2-carboxylic acid has been obtained by transesterification in basic medium using primary, secondary, and tertiary alcohols. Methods of transesterification using various bases (K2CO3, ROLi, t-BuOK) have been compared. Transesterification with lithium alcoholates also affords the possibility of obtaining esters of N-substituted aziridine-2-carboxylic acids. Transesterification of chiral esters proceeds with retention of the configuration of the chiral center. 相似文献
18.
Anna Kryshchyshyn-Dylevych Myroslav Garazd Andrew Karkhut Sviatoslav Polovkovych 《合成通讯》2020,50(18):2830-2838
AbstractA mild and efficient method for the synthesis of 1-oxo-9H-thiopyrano[3,4-b]indole-3-carboxylic acids and dimerized 3-(4-carboxy-1H-3-indolyl)-2-propenoic acids via alkaline hydrolysis of 3-(rhodanin-5-yl)-1H-indole-2-carboxylic acids derivatives was elaborated. Anticancer activity screening in NCI60-cell lines assay allowed identification of 5-fluoro-3-(4-oxo-2-thioxothiazolidin-5-ylidenemethyl)-1H-indole-2-carboxylic acid methyl ester 2a with significant antimitotic activity at micromolar and submicromolar concentrations. 相似文献
19.
Pranesh Kumar Atul Rawat Amit K. Keshari Ashok K. Singh Siddhartha Maity Arnab De 《Natural product research》2016,30(4):460-463
The present study was undertaken to investigate the antiproliferative action of isolated M1 (6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid) from Mucuna pruriens seeds using human hepatic carcinoma cell line (Huh-7 cells). Initially, docking studies was performed to find out the binding affinities of M1 to caspase-3 and 8 enzymes. Later, cytotoxic action of M1 was measured by cell growth inhibition (MTT), followed by caspase-3 and 8 enzymes assay colorimetrically. Our results collectively suggested that M1 had strong binding affinity to caspase-8 in molecular modelling. M1 possessed antiproliferative activity on Huh-7 cells (EC50 = 13.97 μM) and also inhibited the action of caspase-8 enzyme, signified process of apoptosis. M1 was active against Huh-7 cells that may be useful for future hepatic cancer treatment. 相似文献
20.
The 1,2,3,4-tetrahydro-N-pivaloyl-isoquinoline-3-carboxylic acids 1d , 2d , and 3d , derived from (R)- or (S)-phenylalanine, (S)-dopa, and (S)-α-methyldopa, respectively, are doubly deprotonated with (tert-butyl)lithium in THF and alkylated at the 1-position (products 5 – 10 ). The major diastereoisomers formed are the result of electrophilic attack from the face opposite to the carboxylate group (rel. topicity ul-1,3). Even the addition to benzaldehyd (→ 7,8 ) is highly stereoselective (one of four diastereoisomers is formed exclusively (300-MHz 1H-NMR analysis)), if MgBr2 etherate is added prior to the electrophile. Some of the obtained amino-acid derivatives are decarboxylated by anodic oxidation in MeOH (→ 11 , 12 , 17 ) and NaBH3CN reduction, and converted to the known 1-methyl- and 1-benzyltetrahydroisoquinolines ( 15 , 16 ) of > 95% ee as well as to the phthalide isoquinoline alkaloid (+)-corlumine of ≥80% ee. The synthetic approach described here is compared with other methods of synthesizing enantiomerically pure 1-substituted tetrahydroisoquinolines (and thus an important group of alkaloids, Scheme 1). 相似文献