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1.
R. Nurdinov É. É. Liepin'sh I. B. Mazheika I. Ya. Kalvin'sh 《Chemistry of Heterocyclic Compounds》1993,29(10):1215-1221
By the interaction of hydrazides of L-proline, L-thioproline, pipecolic acid, and tetrahydro-1,4-thiazine-3-carboxylic acid with an excess of a carbonyl compound, through a stage of hydrazone formation, the following compounds have been obtained: 2,3-substituted 1,3-diazabicyclo[3.3.0]octan-4-ones; 7,8-substituted 7-thia-1,7-diazabicyclo[3.3.0]octan-6-ones; and 8,9-substituted diazabicyclo[4.3.0]nonan-7-ones. Preferential translinkage of the rings is characteristic for these heterocycles in solutions; if the substitution is asymmetric, the E-isomers are predominant.For Communication 1 see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1415–1421, October, 1993. 相似文献
2.
6-Phenoxyacetamido-8-oxo-1,3-diazabicyclo [4.2.0] octane-2-carboxylic acids have been synthesised and shown to posses weak antibacterial activity. 相似文献
3.
Michael J. Pearson 《Tetrahedron letters》1982,23(29):2999-3002
4-Methoxycarbonylmethylene-6-phenoxyacetamido-7-oxo-1,3-diazabicyclo[3.2.0]heptane-2-carboxylic acid and 4,7-dioxo-6-phenoxyacetamido-1,3-diazabicyclo[3.2.0]heptane-2-carboxylic acid have been prepared. 相似文献
4.
5.
Golnaz Parhizkar Ahmad Reza Khosropour Iraj Mohammadpoor-Baltork Elahehnaz Parhizkar Hadi Amiri Rudbari 《Tetrahedron》2017,73(11):1397-1406
1-Azabicyclo[3.3.0]oct-3-en-2-one derivatives were synthesized efficiently through the facile cascade reaction of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) with arylidene azlactones. This research provides a straightforward procedure for the synthesis of a novel class of multicyclic semi-alkaloids which shows good antimicrobial activity. Under catalyst-free, mild, and solventless condition, a wide range of fused tricyclic derivatives was obtained in high yields. 相似文献
6.
Synthesis and total 1H- and 13C-NMR assignment of cephem derivatives for use in ADEPT approaches 总被引:1,自引:0,他引:1
Blau L Menegon RF Ferreira EI Ferreira AG Boffo EF Tavares LA Heleno VC Chung MC 《Molecules (Basel, Switzerland)》2008,13(4):841-854
We report the synthesis and total NMR characterization of 5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid-3-[[[(4'-nitrophenoxy)carbonyl]oxy]-methyl]-8-oxo-7-[(2-thienyloxoacetyl)amino]-diphenylmethyl ester-5-dioxide (5), a new cephalosporin derivative. This compound can be used as the carrier of a wide range of drugs containing an amino group. The preparation of the intermediate product, 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid-3-[methyl 4-(6-methoxyquinolin-8-ylamino)pentylcarbamate]-8-oxo-7-[(2-thienyloxoacetyl)amino]-diphenylmethyl ester-5-dioxide (6), as well as the synthesis of the antimalarial primaquine prodrug 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid-3-[methyl 4-(6-methoxyquinolin-8-ylamino)pentylcarbamate]-8-oxo-7-[(2-thienyloxoacetyl)amino]- 5-dioxide (7) are also described, together with their total (1)H- and (13)C-NMR assignments. 相似文献
7.
R. Nurdinov E. E. Liepin'sh I. Ya. Kalvin'sh 《Chemistry of Heterocyclic Compounds》1993,29(11):1347-1351
By the interaction of L-proline, L-thioproline, pipecolic acid, tetrahydro-1,4-thiazine-3-carboxylic acid, and diastereomeric esters of tetrahydro-1,4-thiazine-3,5-dicarboxylic acid with methyl chloroformate, methyl propiolate, and acetylenecarboxylic acid, we have obtained N-alkoxycarbonyl and N-alkoxycarbonylalkenyl derivatives of -iminocarboxylic acids. By the reaction of N-methoxycarbonyltetrahydro-1,4-thiazine-3-carboxylic acid with hydrazine hydrate, we have obtained 8-amino-7,9-dioxo-4-thia-1,8-diazabicyclo[4.3.0]nonane.For communication 2, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1561–1566, November, 1993. 相似文献
8.
M. Vorona I. Potorocina G. Veinberg I. Shestakova I. Kanepe E. Lukevics 《Chemistry of Heterocyclic Compounds》2008,44(6):739-749
Sulfones of the tert-butyl esters of 7-arylmethylene-and 7-(2-furyl)methylene-3-methyl-3-cepheme-4-carboxylic acid were obtained by the condensation of the tert-butyl ester of 3-methyl-7-oxo-3-cepheme-4-carboxylic acid with arylmethylene-and 2-furylidenetriphenylphosphoranes and subsequent oxidation of the intermediate products by meta-chloroperbenzoic acid. The combination of the tert-butyl esters of 7E-bromomethylene-and 7,7-dibromomethylene-3-methyl-1,1-dioxo-3-cepheme-4-carboxylic acids with trimethylsilylacetylene under conditions of the Sonogashira reaction gave the tert-butyl esters of 3-methyl-1,1-dioxo-7E-(3-trimethylsilyl-2-propynylidene)-3-cepheme-4-carboxylic acid and 3-methyl-1,1-dioxo-7-[1,5-bis(trimethylsilyl)-1,4-pentadiyn-3-ylidene]-3-cepheme-4-carboxylic acid. The Vilsmeier reagent was used to incorporate the dimethylaminomethylene group at C-2 of the 7Z-and 7E-isomers of the tert-butyl ester of 7-(4-chlorophenyl)methylene-3-methyl-1,1-dioxo-3-cepheme-4-carboxylic acid. The cytotoxic properties of the derivatives of the tert-butyl ester of 7-alkylidene-3-methyl-3-cepheme-4-carboxylic acid in regard to cancer and normal cells in vitro depends on the structure and 7Z-or 7E-isomerism of the substituent in the 7-alkylidene group as well as the presence of a dimethylaminomethylene group at C-2 of the 3-cepheme system. 相似文献
9.
G. A. Gazieva Yu. V. Nelyubina A. N. Kravchenko K. A. Lysenko N. G. Kolotyrkina P. A. Belyakov A. A. Korlyukov O. V. Lebedev N. N. Makhova 《Russian Journal of Organic Chemistry》2009,45(2):248-255
Derivatives of a new heterocyclic system, 3,3′-bi(6,8-dialkyl-2,4-dioxa-7-thia-6,8-diazabicyclo[3.3.0]-octane-7,7-dioxides), were synthesized by condensation of 1,3-dialkylsulfamides with glyoxal (as a dihydrate trimer). Their structure was investigated by spectral methods, XRD, and X-ray phase analysis of one among these compounds. 相似文献
10.
K. V. Kudryavtsev 《Russian Journal of Organic Chemistry》2010,46(3):372-379
cis-5-Arylpyrrolidine-2,4-dicarboxylic acid monoamides undergo thermal intramolecular condensation with formation of bicyclic
imides having a 3,6-diazabicyclo[3.2.1]octane skeleton. The use of copper(I) cyanide as catalyst ensures high yields of 3,6-diazabicyclo[3.2.1]octane-2,4-diones
substituted at the 3-, 5-, 6-, and 7-positions. (1R*,5R*,7S*)-7-(4-Chlorophenyl)-5,6-dimethyl-3,6-diazabicyclo[3.2.1]octane-2,4-dione was found to inhibit thrombin in a buffer solution
at a millimolar concentration. 相似文献
11.
The thermolysis of (Z)-methyl 3-(6-azido-3-chloro-1-methyl-4-oxo-1,4-dihydropyridazin-5-yl)-2-methylacrylate ( II ) provides a new synthetic route to pyrrolo[2,3-c-]pyridazines, specifically, methyl 3-chloro-1,6-dimethyl-4-oxo-1,4-dihydro-7H-pyrrolo[2,3-c]pyridazine-5-carboxylate ( III ) in 91% yield. Treatment of III with ozone provides an entry into the novel pyridazino[3,4-d][1,3]oxazine ring system, specifically, 3-chloro-1,7-dimethylpyridazino[3,4-d][1,3]oxazine-4,5-dione ( IV ) in 73% yield. Compound IV is smoothly hydrolyzed into 6-acetylamino-3-chloro-1-methyl-4-oxo-1,4-dihydropyridazine-5-carboxylic acid ( V ) which is readily recyclized into IV by dehydration with acetic anhydride. Furthermore, IV undergoes a facile reductive ring opening reaction with sodium borohydride to give 3-chloro-6-ethylamino-1-methyl-4-oxo-1,4-dihydropyridazine-5-carboxylic acid ( VI ) in 95% yield. 相似文献
12.
A. N. Pudovik V. K. Khairullin M. A. Vasyanina I. K. Pokrovskaya O. N. Kataeva I. A. Litvinov V. A. Naumov 《Russian Chemical Bulletin》1990,39(11):2345-2348
Sodium salts of 2, 2-dimethyl-4-mercapto-5-oxo-1,3-thiazoline and 2-oxo-3-mercapto-1-thia-4-azaspiro[4.5]dec-3-ene, obtained from a solvate of sodium cyanodithioformate with three molecules of dimethylformamide, acetone, or cyclohexanone in the presence of morpholine, react with chlorothioformic dimethylamide with the formation of 2,2-dimethyl-5-oxo-4-(dimethylaminothiocarbonylthio)-1,3-thiazoline and 2-oxo-3-(dimethylaminothiocarbonylthio)-1-thia-4-azaspiro[4.5]dec-3-ene, respectively, and during acidolysis by hydrochloric acid they are converted to 2,2-dimethyl-5-oxo-4-thiono-1,3-thiazolidine and 2-oxo-3-thiono-1-thia-4-azaspiro[4.5]decane. The latter compounds are facilely phosphorylated by dialkyl chlorophosphonates at the nitrogen atom. The reaction of the solvate of sodium cyanodithioformate with three molecules of dimethylformamide with chloroacetone in the presence of morpho-line occurs anomalously with the formation of cyanothioformic morpholide.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2590–2593, November, 1990. 相似文献
13.
Methyl 2-allyl-3-oxo-2,3-dihydrothiophene-2-carboxylate ( 2 ) photocyclizes selectively to methyl 2-oxo-7-thiatricyclo[3.2.1.03,6]octane-1-carboxylate ( 4 ). In contrast, 4-thia-2-cyclohexenone 3 , on irradiation, affords only low yields of dimers, cycloadducts (2-methylpropene) or RH reduction products (i-ProH). 相似文献
14.
The activity of pharmacologically active compounds can be increased by presenting a drug in a defined conformation, which fits exactly into the binding pocket of its target. Herein, the piperazine scaffold was conformationally restricted by substituted C2- or C3-bridges across the 2- and 6-position. At first, a three-step, one-pot procedure was developed to obtain reproducibly piperazine-2,6-diones with various substituents at the N-atoms in high yields. Three strategies for bridging of piperazine-2,6-diones were pursued: 1. The bicyclic mixed ketals 8-benzyl-6-ethoxy-3-(4-methoxybenzyl)-6-(trimethylsilyloxy)-3,8-diazabicyclo[3.2.1]octane-2,4-diones were prepared by Dieckmann analogous cyclization of 2-(3,5-dioxopiperazin-2-yl)acetates. 2. Stepwise allylation, hydroboration and oxidation of piperazine-2,6-diones led to 3-(3,5-dioxopiperazin-2-yl)propionaldehydes. Whereas reaction of such an aldehyde with base provided the bicyclic alcohol 9-benzyl-6-hydroxy-3-(4-methoxybenzyl)-3,9-diazabicyclo[3.3.1]nonane-2,4-dione in only 10 % yield, the corresponding sulfinylimines reacted with base to give N-(2,4-dioxo-3,9-diazabicyclo[3.3.1]nonan-6-yl)-2-methylpropane-2-sulfinamides in >66 % yield. 3. Transformation of a piperazine-2,6-dione with 1,4-dibromobut-2-ene and 3-halo-2-halomethylprop-1-enes provided 3,8-diazabicyclo[3.2.1]octane-2,4-dione and 3,9-diazabicyclo[3.3.1]nonane-2,4-dione with a vinyl group at the C2- or a methylene group at the C3-bridge, respectively. Since bridging via sulfinylimines and the one-pot bridging with 3-bromo-2-bromomethylprop-1-ene gave promising yields, these strategies will be exploited for the synthesis of novel receptor ligands bearing various substituents in a defined orientation at the carbon bridge 相似文献
15.
Treatment of ethyl 4-aryl-6-(trifluoromethyl)-2-oxo-2H-pyran-3-carboxylates, prepared from 4,4,4-trifluorobutane-1,3-diones, PCl5 and sodium diethyl malonate, with sulfuric acid afforded the intramolecular Friedel–Crafts acylation products, 3-(trifluoromethyl)indeno[2,1-c]pyran-1,9-diones, from which 2-(trifluoromethyl)-6H-pyrano[3,4-c]quinoline-4,5-diones were obtained via the Schmidt reaction in moderate yields. The latter reacted with sodium azide to give 2-oxo-4-(5-trifluoromethyl-1,2,3-triazol-4-yl)-1,2-dihydroquinoline-3-carboxylic acids in good yields. 相似文献
16.
é. B. Shamuratov A. S. Batsanov Yu. T. Struchkov A. Yu. Tsivadze M. G. Tsintsadze L. I. Khmel'nitskii Yu. A. Simonov A. A. Dvorkin O. V. Lebedev T. B. Markova 《Chemistry of Heterocyclic Compounds》1991,27(7):745-749
Isomeric 2,6- and 2,8-diethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-diones were obtained by the reaction of glyoxal with ethylurea, and their crystal structures and IR, Raman, and PMR spectra were studied.Translated from Khimiya Geterotsikiicheskikh Soedinenii, No. 7, pp. 937–941, July, 1991. 相似文献
17.
Kravchenko A. N. Maksareva E. Yu. Belyakov P. A. Sigachev A. S. Chegaev K. Yu. Lyssenko K. A. Lebedev O. V. Makhova N. N. 《Russian Chemical Bulletin》2003,52(1):192-197
New (1R*,5S*)-2-R-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-diones containing the terminal carboxy or hydroxy group in the substituent R were synthesized by cyclocondensation of 4,5-dihydroxyimidazolidin-2-one with 1-R-ureas. Single-crystal X-ray diffraction analysis showed that 2-carboxyethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione crystallizes as a racemate. 相似文献
18.
Esters of substituted 2,3,7-triazabicyclo[3.3.0]oct-3-ene-4-carboxylic acids react with acetone in the presence of hydrogen chloride (bromide) affording esters of substituted 2-(1,1-dimethyl-3-oxobutyl)-2,3,7-triazabicyclo[3.3.0]oct-3-ene-4-carboxylic acids. Reactions of esters of substituted 2,3,7-triazabicyclo[3.3.0]octa-1(5),3-diene-4-carboxylic acids with 1-adamantanol in trifluoroacetic acid resulted in esters of substituted 2-(1-adamantyl)- 2,3,7-triazabicyclo[3.3.0]octa-1(5),3-diene-4-carboxylic acids.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 2, 2005, pp. 252–263.Original Russian Text Copyright © 2005 by Stepakov, Molchanov, Kostikov. 相似文献
19.
Shchepin V. V. Fotin D. V. Nedugov A. N. Fotin V. V. 《Russian Journal of Organic Chemistry》2002,38(2):256-258
Methyl 2-bromo-2-methylpropionate reacts with zinc and arylglyoxals under conditions of Reformatsky reaction in ether-HMPA mixture to afford 1-aryl-4,4,8,8-tetramethyl-2,6-dioxabicyclo[3.3.0]octane-3,7-diones in 68-85% yield. Methyl 2-bromopropionate reacts with zinc and 4-bromophenylglyoxal in the same way giving the bicyclic product in 28% yield. The bromination of 1-(4-tolyl)-4,4,8,8-tetramethyl-2,6-dioxabicyclo[3.3.0]octane-3,7-dione with bromosuccinimide results in successive replacement of hydrogens in the tolyl moiety by bromine. The calculation of formation enthalpy for stereoisomers of compounds obtained in AM1 approximation predicts the highest stability for chair-type conformation with eclipsed position of substituents at C1 and C5 atoms. 相似文献
20.
(S,S,S)-2-Azabicyclo[3.3.0]octane-3-carboxylic acid 1, a structural element of the very potent ACE inhibitor HOE 498, is readily available via a diastereo selective synthesis starting from serine or cystine. 相似文献