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1.
V. V. Shchepin P. S. Silaichev Yu. G. Stepanyan M. M. Kalyuzhnyi N. Yu. Russkikh M. I. Kodess 《Russian Journal of Organic Chemistry》2006,42(7):973-980
Zinc enolates derived from 1-aryl-2,2-dibromoalkanones react with N-substituted 3-aryl-2-cyanoprop-2-enamides and 5,5-dimethyl-2-oxo-2,5-dihydrofuran-3-carboxylic and 2-oxochromene-3-carboxylic acid derivatives to give, respectively, N-substituted 2-alkyl-3-aryl-2-aroyl-1-cyanocyclopropane-1-carboxamides, 6-(4-bromobenzoyl)-4,4,6-trimethyl-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester and morpholide, and 1-alkyl-1-aroyl-2-oxo-1a,7b-dihydrocyclopropla[c]chromene-1a-carboxylic acids as a single geometric isomer. Treatment of 1-alkyl-1-aroyl-2-oxo-1a,7b-dihydrocyclopropa[c]chromene-1a-carboxylic acids with carboxylic acid anhydrides leads to the formation of the corresponding 9c-alkyl-1-aryl-3,4-dioxo-9b,9c-dihydro-2,5-dioxacyclopenta[2,3]cyclopropa[1,2-a]naphthalen-1-yl carboxylates. 相似文献
2.
T. V. Anis’kova V. V. Chadina A. Yu. Yegorova 《Chemistry of Heterocyclic Compounds》2009,45(12):1460-1463
Syntheses were developed for 4-aryl-6-ethoxy-2-R-furo[2,3-b]pyridine-5-carbonitriles and ethyl esters of 5-amino-4-aryl-7-methyl-2-R-1,9-dioxa-8-azacyclopenta[b]naphthalene-6-carboxylic
acids based on the reaction of 6-amino-4-aryl-2-R-4H-furo[2,3-b]pyran-5-carbonitriles with ethyl acetoacetate and nucleophilic
recyclization. The mechanisms of these reactions are considered. 相似文献
3.
V. V. Shchepin P. S. Silaichev Yu. G. Stepanyan N. Yu. Russkikh M. I. Vakhrin M. A. Ezhikova M. I. Kodess 《Russian Journal of Organic Chemistry》2006,42(11):1625-1629
Organozinc compounds prepared from bromomalonic acid esters and zinc react with 3-aryl-2-cyanopropenoic acid primary amides giving a single diastereomer of the corresponding 1-R′-4-aryl-2,6-dioxo-5-cyanopiperidine-3-carboxylic acid esters, or 3-R′-6-aryl-2,4-dioxo-5-cyano-3-azabicyclo[3.1.0]hexene-1-carboxylic acid esters. 相似文献
4.
Triethylamine catalyzes the reaction of 2-hydroxybenzonitrile ( 1 ) with aryl isocyanates to form the corresponding carbamates 2a-c , as well as the cyclization of the latter compounds to either 4[N-(N-arylcarbamoyl)-imino]-3-aryl-2H-1,3-benzoxazin-2-ones 4a-c , or 4-arylamino-2H-1,3-benzoxazin-2-ones 7a-c , depending on the reaction temperature. Under analogous conditions, the carbamates obtained from 1 and 2-chloroethyl isocyanate, 3-chloropropyl isocyanate and ethyl isocyanatoacetate undergo a double cyclization yielding imidazo- and pyrimido[1,2-c|1,3]benzoxazinones 13a,b,17 . Upon heating in phenyl ether, compounds 7a-c , rearrange to 2-(2-hydroxyphenyl)-4(3H)-quinazolinones 10a-c . 相似文献
5.
3-Oxo-3-phenyl-2-(p-tolylhydrazono)propanal (1a) undergoes condensation with ethyl cyanoacetate in acetic acid in the presence of ammonium acetate to yield either 2-hydroxy-6-phenyl-5-p-tolylazonicotinic acid ethyl ester (6a) or 2-amino-6-phenyl-5-ptolyl-azonicotinic acid ethyl ester (8), depending on the reaction conditions. Similarly, other 3-oxo-3-aryl-2-arylhydrazonopropanals 1a,b condense with active methylene nitriles 2c,d to yield arylazonicotinates 6b,c. In contrast, 2-[(4-nitrophenyl)-hydrazono]-3-oxo-3-phenyl-propanal (1c) reacts with ethyl cyanoacetate to yield ethyl 6-(4-nitrophenyl)-2-oxo-2,6-dihydropyrido[3,2–c]cinnoline-3-carboxylate (11), via a novel 6π-electrocyclization pathway. Finally, 3-oxo-2-(phenylhydrazono)-3-p-tolylpropanal (1d) condenses with 2a-c to yield pyridazinones 13a-c. 相似文献
6.
Konstantinos E. Litinas Demetrios N. Nicolaides Evangelia A. Varella 《Journal of heterocyclic chemistry》1990,27(3):769-774
Regioselective 1,3-dipolar cycloaddition of nitrile oxides 5a-c to ethyl o-hydroxycinnamate (3) gave the corresponding ethyl trans-3-aryl-4,5-dihydro-5-(2-hydroxyphenyl)-4-isoxazolecarboxylates 6a-c . Their structure was confirmed by reductive cleavage to 1 and compounds 9a-c . Compounds 6a-c afforded upon heating in the presence of pyridine the 3-aryl-4H-[1]benzopyrano[3,4-d]isoxazol-4-ones 11a-c . Compound 10c was also isolated from 6c and transformed thermally into 11c . 相似文献
7.
N-Arylisoindolines 1a-c reacted with (2,4, 7-trinitro-9H-fluoren-9-ylidene)propanedinitrile ( A ) in pyridine with admission of air via a net α-H-atom abstraction and formation of [3-(2-aryl-3-arylimino-2,3-dihydro- 1H-isoindol-1-ylidene)-2-aryl-2,3-dihydro-1H-isoindol-1-ylidene]propanedinitriles 2a-c , N-[2-aryl-3-(2-aryl-3-arylimino-2,3-dihydro-1H-isoindolyl-1-idene)-2,3-dihydro-1H-isoindol-1-ylidene]arenamines 3a, b , N, N'-[2-aryl-1H-isoindole-1,3(2H)-diylidene]bisarenamines 4a, b and N-arylphthalimides 5a-c in moderate yields. 2,4,7-Trinitro-9-fluorenone as well as one reduction product each of the latter and of A, namely compounds 6 and 7 , respectively, are also found. The structure of 2b has been unambiguously confirmed by an X-ray crystal structure analysis. A rationale for the conversions observed is presented. These involve dehydrogenation and oxidative couplings of 1a-c as well as transfer of N-aryl fragment from 1a-c to intermediate products. 相似文献
8.
Al-Huniti MH El-Abadelah MM Zahra JA Sabri SS Ingendoh A 《Molecules (Basel, Switzerland)》2007,12(3):497-503
Model tetrahydropyrido[3',2':4,5]thieno[2,3-b][1,4]thiazines 9a-c were synthesized via reductive lactamization, using sodium dithionite, of the respective 2-[(carboxyalkyl)thio]-3-nitro-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acids 7a-c. The latter derivatives were made via interaction of 2-chloro-7-cyclopropyl-3-nitro-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid (6) with each of alpha-mercaptoacetic, alpha-mercaptopropionic, and alpha-mercaptosuccinic acids and triethylamine in aqueous acetone at room temperature. The structures of 7a-7c and 9a-9c are supported by microanalytical and spectral (IR, MS, NMR) data. Compounds 9a and 9c showed potent inhibitory activity against the IGROV1 (Ovarian Cancer) cell line. 相似文献
9.
M. Mercedes Blanco Isabel A. Perillo Celia B. Schapira 《Journal of heterocyclic chemistry》1999,36(4):979-984
A number of 8-hydroxy-6-methyl-1,6-naphthyridin-5(6H)-one-7-carboxylic acid alkyl esters 3 and the isomeric 5-hydroxy-7-methyl-1,7-naphthyridin-8(7H)-one-6-carboxylic acid alkyl esters 4 were synthesized from acyclic precursors obtained starting from quinolinic anhydride 5. Thus, methanolysis of 5 afforded the hemiester 6 which treated with oxalyl chloride and sarcosine ethyl ester gave 3-(N-ethoxycarbonylmethyl-N-methylcarbamoyl)pyridine-2-carboxylic acid methyl ester 8. Compound 8 was cyclized to naphthyridines 3a-e with sodium alkoxides. The isomeric naphthyridines 4a-c were obtained by cyclization of the open intermediary 2-(N-ethoxycarbonylmethyl-N-methylcarbamoyl)pyridine-3-carboxylic acid methyl ester 9 obtained by a route that involves treatment of 5 with sarcosine ethyl ester and esterification with diazomethane. Spectroscopic properties (1H nmr, uv, ir) of compounds 3 and 4 are discussed and confirmed the proposed structures. 相似文献
10.
A new approach to the 2H-pyrano[3,2-c]pyridine system is described. 5,6-Disubstituted 3-benzoylamino-2H-pyran-2-ones 3a,b , prepared from the corresponding 1,3-dicarbonyl compounds 1a,b and methyl (Z)-2-benzoylamino-3-dimethylaminopropenoate ( 2 ), were converted into 3-benzoylamino-6-(2-dimethylamino-1-ethenyl)-5-ethoxycarbonyl-2H-pyran-2-one ( 4a ) and 5-acetyl derivative 4b . The exchange of the dimethylamino group in 4a,b with aromatic amines 5a-f,m , héteroaromatic amines 5g-i , and benzylamines 5j-l produced 5-ethoxycarbonyl-3-benzoylamino-6-(2-arylamino- or heteroarylamino-or benzylamino-1-ethenyl)-2H-pyran-2-ones 6a-l , and its 5-acetyl analog 6m . The compounds 6 were cyclized in basic media into 2H-pyrano[3,2-c]pyridine derivatives 7a-h . Analogously react also α-amino acid derivatives 8a-c and 11 as nitrogen nucleophiles producing 9a-c, 10 and 12 . 相似文献
11.
2-Aryl-4-methoxy-9-oxocyclohepta[b]pyrylium perchlorates 1a-c reacted with hydroxylamine hydrochloride and hydrazine sulfate in the presence of triethylamine to afford 2-aryl-4,9-dihydrocyclohepta[b]pyran-4,9-dione 4-oximes 3a-c and 4-hydrazones 4a-c in good yields, respectively. On the other hand, the reactions with methylhydrazine and phenylhydrazine gave respectively 1-methyl- and 1-phenyl-substituted 5-aryl-3-(3-tropolonyl)pyrazoles 5a-c and 6a-c in excellent yields. Treatment with 4-nitrophenylhydrazine gave 2-aryl-4,9-dihydrocyclohepta[b]pyran-4,9-dione 4-(4-nitrophenyl)hydrazones 7a-c in good yields. 相似文献
12.
13.
E. V. Nosova L. P. Sidorova G. N. Lipunova N. N. Mochul'skaya O. M. Chasovskikh V. N. Charushin 《Chemistry of Heterocyclic Compounds》2002,38(8):922-928
Ethyl esters of 1-(7-Z-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carbamoyl)-5-X-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acids (X = H, F; Z = pyrrolidino-, piperidino-, hexamethylenimino-, morpholino-, thiomorpholino-) have been synthesized by the interaction of quinolone-3-carboxylic acid hydrazides with ethyl esters of 3-ethoxy-2-(polyfluorobenzoyl)acrylic acid . It was shown possible to cyclize intramolecularly the esters obtained with the formation of 1,3,4-oxadiazino[6,5,4-i,j]quinoline derivatives. 相似文献
14.
Vladimir L. Rusinov Grigori V. Zyryanov Tatjana L. Pilicheva Oleg N. Chupakhin Hans Neunhoeffer 《Journal of heterocyclic chemistry》1997,34(3):1013-1019
3-Aryl-1,2,4-triazin-5(2H)-ones 1a-c react with indoles 2a-c in trifluoroacetic acid/chloroform or in boiling butanol or acetic acid to give 3-aryl-6-(indolyl-3)-1,6-dihydro-1,2,4-triazin-5(2H)-ones 3a-g . Oxidation of the dihydro-1,2,4-triazin-5(2H)-ones 3a-e afforded 6-(indolyl-3)-1,2,4-triazin-5(2H)-ones 4a-e , products of nucleophilic substitution of hydrogen in 1a-c . Refluxing 1b with N-methylpyrrote 5b in butanol for an extended time resulted in the formation of 3-(4-chlorophenyl)-6-(1-meuiylpyrrolyl-2)-1,2,4-triazin-5(2H)-one 4h. The reaction of 1a-c with indoles 2a-c , pyrroles 5a,b , 1,3-dimethyl-2-phenylpyrazol-4-one (8) and aminothiazoles 9a,b in acetic anhydride affords the 1-acetyl-3-aryl-6-hetaryl-1,6-dihydro-1,2,4-triazin-5(2H)-ones 6a-s . Reaction of 1a-c with N-methyl-pyrrole 5b in acetic anhydride gives beside the 1:1 addition products 6h-k also the 2:1 addition products 7a-c . 相似文献
15.
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
16.
G. Dattolo G. Cirrincione A. M. Almerico I. D'Asdia E. Aiello 《Journal of heterocyclic chemistry》1982,19(5):1237-1239
A new synthesis of 2-methyl-9-R'-10-R-5,6-dihydro-7H-pyrazolo[1,5-d][1,4]benzodiazepin-6-ones ( 4a-c ) is deserved. Reaction of ethyl hydrazinoacetate hydrochloride with 1,3-diketones 1a-c gave both 3-methyl-5-(4R'-5-R-2-nitrophenyl)pyrazol-1-yl-acetate acids ( 2a-c ) and the corresponding ethyl esters 3a-c . Reduction with the appropiate reducing agent of compounds 2a-c and 3a-c directly gave the title compounds. Compound 4a showed insecticidal properties against the house fly. 相似文献
17.
3-Acetyltropolone ( 1 ) reacted with benzaldehydes in trimethyl orthoformate in the presence of perchloric acid to afford 2-aryl-4-methoxy-9-oxocyclohepta[b]pyrylium perchlorates 3a-c in 25–37% yields. From the filtrates, 3-(3,4-diaryl-3-butenoyl)tropolones 4a,b and 3-(2-methoxycinnamoyl)tropolone ( 5 ) were also isolated. 相似文献
18.
P Bongen J Pietruszka RC Simon 《Chemistry (Weinheim an der Bergstrasse, Germany)》2012,18(35):11063-11070
An efficient asymmetric synthesis of (S)-2,3-dihydrobenzo[b]furan-3-carboxylic acid (8?a) and (S)-5-chloro-2,3-dihydrobenzo[b]furan-3-carboxylic acid (8?b) was established. Key to the success was the highly stereoselective enzymatic kinetic resolution of the corresponding methyl or ethyl esters that was further developed into a dynamic process. As a reliable and fast tool for analysing the enantiomeric excess, HPLC coupled with a CD detector was utilized. The route was completed by a Friedel-Crafts acylation of ethyl (S)-5-chloro-2,3-dihydrobenzo[b]furan-3-carboxylate (7?c) followed by saponification leading to (S)-5-chloro-2,3-dihydrobenzo[b]furan-3-carboxylic acid (2), an analgesic agent. 相似文献
19.
V. V. Shchepin A. E. Korzun S. N. Shurov M. I. Vakhrin N. Yu. Russkikh 《Russian Journal of General Chemistry》2004,74(9):1410-1413
Zinc enolates formed from 1-aryl-2-bromoalkanones react with methyl esters of substituted 2-oxochromene-3-carboxylic acids to give methyl esters of 6-bromo- or 6,8-dibromo-4-(2-aryl-2-oxo-1-R- ethyl)-2-oxochromane-3-carboxylic acids as mixtures of two diastereomers.Translated from Zhurnal Obshchei Khimii, Vol. 74, No. 9, 2004, pp. 1520–1523.Original Russian Text Copyright © 2004 by Shchepin, Korzun, Shurov, Vakhrin, Russkikh.This revised version was published online in April 2005 with a corrected cover date. 相似文献
20.
Dong Han Kim Arthur A. Santilli Richard A. Fieber 《Journal of heterocyclic chemistry》1972,9(6):1347-1354
Syntheses of 11-acety1-2-phenylpyrimido[5,4-c][1,5]benzoxazepin-5(11H)one ( 16a ) and analogs ( 16b,c, 22 ) were described. The reaction of 4-chloro-2-phenyl-5-pyrimidinecarboxylic acid ethyl ester ( 7 ) with 2-aminophenol afforded 4-(2-hydroxyanilino)-2-phenyl-5-pyrimidine-carboxylic acid ethyl ester ( 8a ). The latter was also prepared by catalytic reduction of 4-(2-nitrophenoxy)-2-phenyl-5-pyrimidinecarboxylic acid ethyl ester ( 9 ), which was obtained from 7 and 2-nitrophenol. Involvement of 4-(2-aminophenoxy)-2-phenyl-5-pyrimidinecarboxylic acid ethyl ester ( 12a ) in this reduction as an intermediate was demonstrated by an independent synthesis of 12a and its subsequent rearrangement to 8a. Hydrolysis of 8a or 12a gave 4-(2-hydroxyanilino)-2-phenyl-5-pyrimidinecarboxylic acid ( 15a ). Reaction of 15a with acetic anhydride afforded 16a , the first member of a novel ring system, the pyrimido[5,4- c ][1,5]-benzoxazepin. Additional examples ( 16b,c ) were prepared similarly. The corresponding 11-ethyl derivative ( 22 ) was prepared in similar fashion, starting with 7 and 2-ethylaminophenol. A possible reaction mechanism for the formation of 16a-c from 15a-c and acetic anhydride was discussed. 相似文献