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1.
Mutulis F Gogoll A Mutule I Yahorava S Yahorau A Liepinsh E Wikberg JE 《Molecules (Basel, Switzerland)》2008,13(8):1846-1863
Two molecules of indole derivative, e.g. indole-5-carboxylic acid, reacted with one molecule of thiol, e.g. 1,2-ethanedithiol, in the presence of trifluoroacetic acid to yield adducts such as 3-[2-(2-amino-5-carboxyphenyl)-1-(2-mercaptoethylthio)ethyl]-1Hindole-5-carboxylic acid. Parallel formation of dimers, such as 2,3-dihydro-1H,1'H-2,3'-biindole-5,5'-dicarboxylic acid and trimers, such as 3,3'-[2-(2-amino-5-carboxyphenyl) ethane-1,1-diyl]bis(1H-indole-5-carboxylic acid) of the indole derivatives was also observed. Reaction of a mixture of indole and indole-5-carboxylic acid with 2-phenylethanethiol proceeded in a regioselective way, affording 3-[2-(2-aminophenyl)-1-(phenethylthio)ethyl]-1H-indole-5-carboxylic acid. An additional product of this reaction was 3-[2-(2-aminophenyl)-1-(phenethylthio)ethyl]-2,3-dihydro-1H,1'H-2,3'-biindole-5'-carboxylic acid, which upon standing in DMSO-d6 solution gave 3-[2-(2-aminophenyl)-1-(phenethylthio)ethyl]-1H,1'H-2,3'-biindole-5'-carboxylic acid. Structures of all compounds were elucidated by NMR, and a mechanism for their formation was suggested. 相似文献
2.
Summary. All-endo-3-amino-5-hydroxybicyclo[2.2.1]heptane-2-carboxylic acid and two epimers of 3-amino-6-hydroxybicyclo[2.2.1]heptane-2-carboxylic
acid were prepared via 1,3-oxazine or γ-lactone intermediates by the stereoselective functionalization of endo-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylic acid derivatives. Their structures were proved by IR and NMR spectroscopy, with
the use of HMQC, HMBC, DEPT, and DIFFNOE techniques. 相似文献
3.
Márta Palkó Elvira Sándor Pál Sohár Ferenc Fül?p 《Monatshefte für Chemie / Chemical Monthly》2005,4(5):2051-2058
All-endo-3-amino-5-hydroxybicyclo[2.2.1]heptane-2-carboxylic acid and two epimers of 3-amino-6-hydroxybicyclo[2.2.1]heptane-2-carboxylic
acid were prepared via 1,3-oxazine or γ-lactone intermediates by the stereoselective functionalization of endo-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylic acid derivatives. Their structures were proved by IR and NMR spectroscopy, with
the use of HMQC, HMBC, DEPT, and DIFFNOE techniques. 相似文献
4.
Starting from the readily available 2-aminobenzhydrols ( 7 ), 3-amino-1,2,4-benzotriazine ( 11 ) and 2-amino-3-pyridinol ( 12 ), novel derivatives of 5-phenyl-5H-imidazo[1,2-a][3,1]benzothiazine-2-carboxylic acid, ethyl ester ( 4 ), imidazo[2,1-c][1,2,4]benzotriazine-2-carboxylic acid, ethyl ester ( 5 ) and 4H-imidazo[2,3-c]pyrido-[2,3-e][1,4]oxazine ( 6 ) were prepared. 相似文献
5.
V. P. Perevalov L. I. Baryshnenkova K. S. Tsoi 《Chemistry of Heterocyclic Compounds》1992,28(9):1004-1005
In the reaction of 3(5)-amino-5(3)-methylpyrazole with 1-nitroanthraquinone-2-carboxylic acid in sulfolane at 150°C, 2-methyl-pyrazolo[5,1-b]naphtho[2,3-h]quinazoline-5,10,13-trione is formed with an admixture of 1-aminoanthraquinone-2-carboxylic acid and 1-aminoanthraquinone. Under similar conditions, from 4-amino-1,5-dimethylpyrazole, only 1-(1,5-dimethyl-4-pyrazolylamino)anthraquinone-1-carboxylic acid is formed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1191–1192, September, 1992. 相似文献
6.
Wiberg KB 《The Journal of organic chemistry》2002,67(5):1613-1617
The acidities of 3- and 4-substituted bicyclooctane-1-carboxylic acids and 3-substituted bicyclo[1.1.1]pentane-1-carboxylic acids have been calculated at the MP2/6-311++G** theoretical level. There is good agreement between the calculated and observed gas-phase acidities. The acidities of the 4-substituted bicyclooctane acids were found to be linearly dependent on the C-X bond dipoles, as expected from a field effect. The substituents had a negligible effect on the electron density at C1. The difference in acidity between 4-chlorobicyclo[2.2.2]octane-1-carboxylic acid and the parent acid (6.2 kcal/mol) is reproduced by the Kirkwood-Westheimer treatment of substituent effects on acidity, but only if the bicyclooctane ring is given an effective dielectric constant of unity. The acidities of the 3-substituted bicyclooctane acids are linearly related to the corresponding 4-substituted acids with a slope of 0.9. The acidities of the 3-substituted bicyclo[1.1.1]pentane-1-carboxylic acids are linearly related to the C-X bond dipoles for this ring system (which are different than those for the bicyclooctanes), and they are also linearly related to the acidity of the 4-substituted bicyclo[2.2.2]octanecarboxylic acids with a slope of 1.34. The larger slope is due to the smaller bridgehead-bridgehead distance in the bicyclopentane ring than in bicyclo[2.2.2]octane. 相似文献
7.
Rodolfo Nesi Stefano Chimichi Francesco De Sio Mirella Scotton 《Magnetic resonance in chemistry : MRC》1983,21(1):42-45
The 13C NMR spectra of a number of pyridazine derivatives have been recorded in DMSO-d6 solution and analysed. Examination of the most diagnostic resonances, with particular emphasis on those arising from the pyridazine ring system, enabled the ready establishment of the presence of a ring-chain tautomerism in 5-(o-aminophenylcarbamoyl)pyridazine-4-carboxylic acid, methyl 5-(o-aminophenylcarbamoyl)pyridazine-4-carboxylate, 5-(o-aminophenylcarbamoyl)-3,6,-dimethylpyridazine-4-carboxylic acid and 5-(2-amino-1,2-dicyanovinylenecarbamoyl)pyridazine-4-carboxylic acid. This gave rise to 3′,4′-dihydro-3′-oxospiro[pyridazine-5(2H),2′(1H)-quinoxaline]-4-carboxylic acid, methyl 3′,4′-dihydro-3′oxospiro[pyridazine-5(2H),2′(1′H)-quinoxaline]-4-carboxylate, 3′,4′-dihydro-3′-oxo-3,6-dimethylspiro[pyridazine-5(2H), 2′(1′H)-quinoxaline]-4-carboxylic acid and 5-oxo-2,3-dicyano-1,4,8,9-tetraazaspiro[5.5]undeca-2,7,10-triene-11-carboxylic acid, respectively. 相似文献
8.
An Ullmann reaction between 2-bromonicotinic acid and 2,6-diaminopyridine gave 6 -amino-2,2 -dipyridylamino-3-carboxylic acid (V). The latter was converted into 7-amino-5H-dipyrido-[1,2-a:2,3 -d]pyrimidin- 5-one (VII) by heating with polyphosphoric acid and into 2-amino-5,10 H-anthyridin-5-one (VIII) by heating with concentrated sulfuric acid. Structure proofs of VII and VIII are given and some derivatives of VIII are described. 相似文献
9.
Etify A. Bakhite Abdu E. Abdel-Rahman Omima. S. Mohamed Eman A. Thabet 《Phosphorus, sulfur, and silicon and the related elements》2013,188(10):1983-2006
(4-Aryl-3-cyano-6-(2-thienyl)pyridin-2-ylthio)acethydrazides (5a–c), 3-amino-4-aryl-6-(2-thienyl)thieno[2,3-b]pyridine-2-carbohydrazides (6a–c) and 3-amino-4-phenyl-6-(2-thienyl)thieno[2,3-b]pyridine-2-carboxylic acid (30) were prepared and employed as key intermediates in the synthesis of the title compounds. 相似文献
10.
Chun Hui Gao Cheng Guo Jia Wei Li Yue Zhang Yi Feng Yu 《Research on Chemical Intermediates》2013,39(8):3911-3917
An efficient chemoenzymatic process has been developed for preparation of 7-amino-3-[Z-2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid, featuring removal of para-methoxybenzyl by trichloroacetic acid and cleavage of phenylacetyl E-isomer by immobilized penicillin acylase enzyme. The E-isomer of 7-amino-3-[Z-2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid could be easily decreased to less than 0.2 % by salt formation. Importantly, trichloroacetic acid and immobilized penicillin acylase enzyme could be recovered and reused. The enzyme reaction could be run in a flow reactor. Only two crystallizations are involved as the purification procedure in the six-step sequence. 相似文献
11.
V. M. Kisel E. O. Kostyrko M. O. Platonov V. A. Kovtunenko 《Chemistry of Heterocyclic Compounds》2002,38(3):300-305
By condensation of 4-(2-bromomethyl)-3,4,5,6-tetrahydro-2H-pyran-4-carbonitrile with anthranilic acid, its derivatives substituted in the benzene ring (esters, nitrile), and with esters of 2-aminothiophene-3-carboxylic acids and 3-amino-5-bromobenzofuran-2-carboxylic acid there have been synthesized novel derivatives which include spiro-linked tetrahydropyran and 5,10-dihydro-3H-pyrimido[1,2-b]isoquinoline fragments. The pyrimidine ring of the latter was annelated by a substituted benzene, thiophene, or 5-bromobenzofuran ring. 相似文献
12.
2-Hydroxymethyl-1,4-diazabicyclo[2.2.2]octane was synthesized by reduction of 1,4-diazabicyclo[2.2.2]octane-2-carboxylic acid or its methyl ester with lithium aluminum hydride in tetrahydrofuran and by hydrolysis or hydrogenation of 2-benzyloxymethyl-1,4-diazabicyclo[2.2.2]octane. Depending on the conditions, 2-hydroxymethyl-1,4-diazabicyclo[2.2.2]octane reacts with methyl iodide to give primarily either a bisquaternary or a monoquaternary derivative. The latter is the only product in its alkylation with methyl esters of benzoic and caproic acids.See [1] for Communication 4.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1404–1407, October, 1980. 相似文献
13.
4-Amino-1, 2, 5-selenadiazole-3-carboxylic acid and 4-amino-1, 2, 5-selenadiazole-3-carboxamides have been prepared by ring-cleavage of [1, 2, 5]selenadiazolo[3, 4-d]pyrimidin-7(6H)-one by basic reagents. The primary amide (III), as well as an N-alkyl amide, may be produced by the action of a primary amine. Hydrazine reductively cleaves the selenadiazole ring. The preparation of similar 4-ureido derivatives by ring-cleavage of [1,2,5]selenadiazolo[3, 4-d]pyrimidine-5, 7(4 H, 6H)-dione has been demonstrated with two examples. N-Butyl-4-ureido-1, 2, 5-selenadiazole-3-carboxamide is easily hydrolyzed in aqueous base to the corresponding acid, and it has been shown that this reaction proceeds by way of [1, 2, 5]selenadiazolo[3,4-d]pyrimidine-5, 7 (4H, 6H)-dione. The 4-amino-1, 2, 5-selenadiazole-3-carboxylic acid derivatives have marked cytotoxic, antibacterial, and antifungal activity. 相似文献
14.
Al-Huniti MH El-Abadelah MM Zahra JA Sabri SS Ingendoh A 《Molecules (Basel, Switzerland)》2007,12(8):1558-1568
Substituted [1,4]thiazepino[2,3-h]quinolinecarboxylic acid 3 is prepared by PPA-catalyzed thermal lactamization of the respective 8-amino-7-[(2-carboxyethyl)thio]-1,4-dihydroquinoline-3-carboxylic acid 9. The latter synthon is obtained by reduction of the 8-nitro-1,4-dihydroquinoline precursor 8 which, in turn, is made accessible via interaction of 3-mercaptopropionic acid with 7-chloro-1-cyclopropyl-6-fluoro-8-nitro-1,4-dihydroquinoline-3-carboxylic acid 7 in the presence of triethylamine. A benzo-homolog of 3, namely tetrahydroquino[7,8-b]benzothiazepine-3-carboxylic acid 6, is analogously prepared via the reaction of 2-mercaptobenzoic acid with 7, followed by reduction of the resulting 7-[(2-carboxyphenyl)thio]-8-nitro product 10 into the corresponding 8-amino derivative 11, and subsequent lactamization. The structures assigned to 3, 6 and 8-11 are based on microanalytical and spectral (IR, MS, NMR) data. 相似文献
15.
Yu. I. Gorak N. D. Obushak V. S. Matiichuk R. Z. Lytvyn 《Russian Journal of Organic Chemistry》2009,45(4):541-550
Arylation of furan-2-carboxylic acid or its methyl ester with arenediazonium chlorides in the presence of copper(II) chloride gave the corresponding 5-arylfuran-2-carboxylic acids or methyl 5-arylfuran-2-carboxylates. 5-Arylfuran-2-carbonyl chlorides reacted with potassium thiocyanate and then with 5-methyl-1,2-oxazol-3-amine to give 5-aryl-N-[3-(2-oxopropyl)-1,2,4-thiadiazol-5-yl]furan-2-carboxamides as a result of recyclization of intermediate isoxazolylthiourea derivatives. The reactions of 5-arylfuran-2-carbonyl chlorides with 5-(2-furyl)-1H-tetrazole involved opening of the tetrazole ring with elimination of nitrogen molecule and led to the formation of 2-(5-arylfuran-2-yl)-5-(2-furyl)-1,3,4-oxadiazoles. 3-Substituted 6-(5-arylfuran-2-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles were obtained by condensation of 5-arylfuran-2-carboxylic acids with 5-substituted 4-amino-4H-1,2,4-triazole-3-thiols in phosphoryl chloride. 相似文献
16.
O. V. Kayukova Ya. S. Kayukov A. N. Nikolaev O. V. Ershov A. V. Eremkin O. E. Nasakin 《Russian Journal of Organic Chemistry》2006,42(4):591-595
The reactions of 6,6-dialkyl-5,7-dioxo-4,8-dioxaspiro[2.5]octane-1,1,2,2-tetracarbonitriles with primary aliphatic alcohols lead to the formation of alkyl 2,2,3,3-tetracyanocyclopropanecarboxylates; the reactions of the same compounds with ketone oximes give 2-amino-4,4-bis(alkylideneaminooxy)-6-(alkylidene-aminooxycarbonyl)-3-azabicyclo[3.1.0]hex-2-ene-1,5-dicarbonitriles, while with aldehyde oximes 2-amino-2-oxo-1,5-dicyano-3-azabicyclo[3.1.0]hex-2-ene-6-carboxylic acid is formed. 相似文献
17.
The successful enantioseparation of five 6-desfluoroquinolones with three polysaccharide-based stationary phases (namely, the cellulose-based Chiralpak IB and the two amylose-based Chiralpak AD-H and Lux Amylose-2) is herein described. The investigated species differ for the nature of substituents and/or the position of the stereogenic centre on the quinolone scaffold.The effect on the enantioseparation performance exerted by the different morphology of the cellulose-based and amylose-based polymers, was systematically evaluated for all compounds. In this frame, the impact of alternative alcoholic (ethanol, 2-ethoxyethanol, methanol, 2-propanol) and acidic (acetic, methanesulfonic and trifluoroacetic acid) modifiers as well as of a “non-standard” solvent (chloroform), was investigated in normal phase conditions along with the stereo-electronic peculiarities of the selected polymers. While 7-[4-(1,3-benzothiazol-2-yl)-2-methyl-1-piperazinyl]-1-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid (1) was enantioresolved with conventional normal-phase conditions by means of the largely employed amylose-based Chiralpak AD-H column, the recruitment of a bulky alcohol (2-ethoxyethanol) succeeded in the enantioresolution of 6-amino-1-methyl-7-[2-methyl-4-(2-pyridinyl)-1-piperazinyl]-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid (2) and 6-amino-1-[1-(hydroxymethyl)propyl]-4-oxo-7-(4-pyridin-2-ylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid (3) with the same column. The use of the amylose-based Lux Amylose-2 column, carrying both an electro-withdrawing (chlorine) and an electro-donating (methyl) group on the carbamate residue, allowed to get 6-amino-1-methyl-4-oxo-7-[3-(2-pyridinyl)-1-pyrrolidinyl]-1,4-dihydro-3-quinolinecarboxylic acid hydrochloride (4) enanantioresolved, and 6-amino-1-methyl-4-oxo-7-(3-pyridin-2-ylpiperidin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid (5) enantioseparated. 相似文献
18.
A. V. Sergievskii O. A. Krasnoshek S. F. Mel'nikova I. V. Tselinskii 《Russian Journal of Organic Chemistry》2002,38(6):872-874
Reactions of 4-aminofurazan-3-carboxylic acid iminoester with o-aminophenol and ethylenediamine give rise respectively to 4-(1,3-benzoxazol-2-yl)- and 1-(4,5-dihydro-1H-imidazol-2-yl)-1,2,5-oxadiazol-3-amines, with aminoethanol arises 2-[(Z)-1-amino-1-(4-amino-1,2,5-oxadiazol-3-yl)methylideneamino]-1-ethanol. Treating of 3-amino-4-(1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazole with triethyl orthoformate in acetic anhydride yielded benzo[4,5]imidazo[1,2-c][1,2,5]oxadiazolo[3,4-e]pyrimidine, and alkylation with haloalkanes furnished 3-amino-4-(1-R-benzo[d]imidazol-2-yl)-1,2,5-oxadiazoles. 相似文献
19.
An efficient and easy formal [2+2] cycloaddition (Michael-Dieckmann-type reaction) on methyl 2-acetamidoacrylate with ketene diethyl acetal gave the cyclobutane core. Two kinds of 2-substituted cyclobutane amino acids have been obtained from this compound by means of stereocontrolled interconversion of functional groups: 1-amino-2-methylcyclobutane-1-carboxylic acids (2,4-methanovalines) and 1-amino-2-methylenecyclobutane-1-carboxylic acid. The latter amino acid can be regarded as a restricted α-methyl-α-vinylglycine. 相似文献
20.
L. B. Mrachkovskaya K. F. Turchin L. N. Yakhontov 《Chemistry of Heterocyclic Compounds》1976,12(8):927-930
1,4-Diazabicyclo[2.2.2]octane-2-carboxylic acid bis(methylbromide), which is readily converted with splitting out of hydrogen bromide to the corresponding quaternary betaine, was synthesized. 相似文献