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1.
Alexander V. Stepakov Maria S. LedovskayaVitaly M. Boitsov Alexander P. MolchanovRafael R. Kostikov Vladislav V. GurzhiyGalina L. Starova 《Tetrahedron letters》2012,53(40):5414-5417
5,8a,11a,11b-Tetrahydroisoxazolo[5′,4′:3,4]pyrrolo[2,1-a]isoquinolin-8(6H)-ones were prepared by intramolecular cyclization of 5-(2-arylethyl)-6-hydroxytetrahydro-4H-pyrrolo[3,4-d]isoxazol-4-ones in the presence of boron trifluoride diethyl etherate. 相似文献
2.
L. M. Gornbstaev G. F. Zeibert G. I. Zolotareva 《Chemistry of Heterocyclic Compounds》1980,16(7):704-707
The behavior of 3,5-dihalo derivatives of anthra[1, 9-c,d]isoxazol-6-one with respect to primary and secondary amines was studied. 5-Chloroanthra[1,9-c,d]isoxazol-6-one undergoes amination particularly readily. The products of the reaction of isoxazoles with amines are the corresponding amino derivatives. The amination of 5-chloroanthra[1,9-c,d] isoxazol-6-one in refluxing dimethylformamide (DMF) is accompanied by reductive cleavage of the isoxazole ring and the formation of 1-amino-4-arylaminoanthraquinones. Amination in the 5 position with substitution of a hydride ion takes place primarily in the reaction of 3-chloroanthra[1,9-c,d]isoxazol-6-one with benzylamine of cyclohexylamine, whereas the chlorine in the 3 position is replaced by the action of morpholine or piperidine on the same substrate.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 912–915, July, 1980. 相似文献
3.
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
4.
The reaction of 2H-thiopyran-3,5(4H,6H)-dione with N,N-dimethylformamide dimethyl acetal gave in good yield 4-dimethylaminomethylene-2H-thiopyran-3,5(4H,6H)dione (II), which afforded 1-substituted 5,7-dihydrothiopyrano[3,4-c]pyrazol-4(1H)-ones with aliphatic and aromatic hydrazines, 5H-thiopyrano[4,3-d]isoxazol-4(7H)-one (IV) with hydroxylamine hydrochloride and 2-substituted 6H-thiopyrano[3,4-d]pyrimidin-5(8H)-ones with amidines and guanidines, generally in satisfactory yields. 4-(t-Butylhydrazonoformyl)-2H-thiopyran-3,5(4H,6H)-dione was isolated as an intermediate in the reaction of II with t-butylhydrazine, whereas formamidine gave with II 4-iminoformyl-2H-thiopyran-3,5(4H,6H)-dione as the sole product. The isoxazole IV isomerized easily with sodium methoxide to 3,4,5,6-tetrahydro-5,5-dihydroxy-3-oxo-2H-thiopyrano-4-carbonitrile. 相似文献
5.
[reaction: see text] Novel and highly efficient syntheses of oxazolo[4,5-c]quinoline-4(5H)-ones (1) and thiazolo[4,5-c]quinoline-4(5H)-ones (2) from ethyl 2-chlorooxazole-4-carboxylate (4) and ethyl 2-bromo-5-chlorothiazole-4-carboxylate (13), respectively, are described. 相似文献
6.
2-Hydroxy-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-4-one 2a and 7-hydroxy-5H-thiazolo[3,2-a]pyrimidin-5-one 2b, were obtained in high yields under mild conditions from the cyclization reactions of bis-(2,4,6-trichlorophenyl) malonate and 2-aminobenzothiazole or 2-aminothiazole, respectively. A new class of compounds, 2,3-dihydro-4H-benzo[4,5]thiazolo[3,2-a]furo[2,3-d]pyrimidin-4-ones and 6,7-dihydro-5H-furo[2,3-d]thiazolo[3,2-a]pyrimidin-5-ones, were synthesized via the microwave assisted radical addition of compounds 2a and 2b to various alkenes using manganese(III) acetate. A preliminary acetylcholine esterase (AchE) inhibition test of compound 4e showed excellent (92%) inhibitory potential, comparable with the standard drug Donapezil®. 相似文献
7.
《Tetrahedron》1987,43(18):4195-4202
Treatment of ethyl (heteroalkylidene)aminopyrazole-4-carboxylates with hydrazine hydrate generally provides a ready synthetic route to 5-amino-4, 5-dihydropyrazolo [3,4-d] pyrimidin-4-ones, although ethyl 5-[(dimethylamino) alkylidene]aminopyrazole-4-carboxylates are unreactive.On the other hand, reactions between aminopyrazole-4-carboxhydrazides and orthoesters or amide acetal are more versatile : we observed formation of isomeric 2-pyrazolyl-1,3,4-oxadiazoles, as major compounds, either from triethyl orthoacetate and 1-methyl-5-aminopyrazole-4-carboxhydrazide or from dimethylacetamide dimethyl acetal and various heterocyclic precursors. The ring closure mechanism is discussed. 相似文献
8.
Chiara B. Vicentini Augusto C. Veronese Maurizio Manfrini 《Journal of heterocyclic chemistry》1997,34(2):629-632
The synthesis of imidazo[4,5-c]pyrazol-5-ones ( 6 ) is reported. 5-Amino-4-ethoxycarbonylaminopyra-zoles 3a-g when heated at 200° for 2 hours afford 6a-g. In a similar manner imidazo[4,5-c]pyrazol-5-one ( 6a ) is readily obtained from 4-amino-5-ethoxycarbonylaminopyrazole ( 5a ). 相似文献
9.
F. A. Amer M. Hammouda A.-A. S. El-Ahl B. F. Abdel-Wahab 《Chemistry of Heterocyclic Compounds》2007,43(12):1559-1566
New pyrrolo[3,4-c]isoxazole derivatives were synthesized from the key intermediates 4-cyanopyrrolidin-3-ones in two steps.
Pyrrolo[2,3-d][1,2,3]triazoles and triazolo[4,5-c]pyridazine were obtained from 2-arylhydrazono-4-cyano-1-(4′-methoxyphenyl)-3-oxopyrrolidines
by refluxing with phenylhydrazine in either ethanol or glacial acetic acid. Aldol self-condensation of 1-aryl-4-cyanopyrrolidin-3-ones
afforded dipyrrolo-[3,2-b:3′, 4′-d]pyran derivatives.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1841–1848, December, 2007. 相似文献
10.
1-Azido-3-phenalenones 5 with acyl substituents in position 2, obtained by acylation and azidation of 1-hydroxy-3-phenalenones 1 , cyclized by thermolysis to give phenaleno[1,2-c]isoxazol-7-ones 9 . The thermolysis conditions were studied by differential scanning calorimetry. 相似文献
11.
Pierfrancesco Bravo Calimero Ticozzi Sergio Daolio Pietro Traldi 《Journal of mass spectrometry : JMS》1985,20(12):740-747
The mass spectrometric behaviour of two pairs of isomeric 2,2-dimethylpyrano[3,2-c][1]benzopyran-5-ones (pyranocoumarins) and 2,2-dimethylpyrano[2,3-b][1]benzopyran-5-ones (pyranochromones) and four pairs of isomeric 2-hydroxymethyl-2-methylpyrano[3,2-c][1]benzopyran-5-ones (pyranocoumarins) and 2-hydroxymethyl-2-methylpyrano[2,3-b][1] benzopyran-5-ones (pyranochromones) has been studied in detail with the aid of exact mass measurements, linked scans, collisionally activated decompositions and deuterium labelling experiments. The presence in both series of compounds of the same ions derived by structural interconversion of both molecular ions is emphasized, and structural information on the ions [C7H5O2]+ (m/z 121), highly characteristic for these classes of compounds, as for 4-hydroxycoumarins, is reported. 相似文献
12.
Anton V. Tverdokhlebov Alexander P. Andrushko Andrey A. Tolmachev Alexander N. Kostyuk Alexander N. Chernega Eduard B. Rusanov 《Monatshefte für Chemie / Chemical Monthly》2005,15(2):1781-1790
Ethyl [4-oxo-3-(2-oxo-2-arylethyl)thiazolidin-2-ylidene]acetates and [4-oxo-3-(2-oxo-2-arylethyl)thiazolidin-2-ylidene]acetonitriles
were shown to react with substituted benzaldehydes at the endocyclic methylene group leading to the corresponding 5-arylmethylidene
derivatives. Their treatment with DMF · POCl3 complex yielded 3-oxo-5-aroyl-2-arylmethylidene-2,3-dihydropyrrolo[2,1-b]thiazole-7-carboxylic acids ethyl esters and -7-carbonitriles. The structures of the pyrrolothiazoles were confirmed by an
X-ray crystallographic study, which indicated the (Z)-configuration at the arylmethylidene moiety. 相似文献
13.
N. I. Astrakhantseva V. G. Zhiryakov P. I. Abramenko 《Chemistry of Heterocyclic Compounds》1975,11(12):1364-1366
2-Mercaptothieno[3,2-d]- and 2-mercaptobenzo[4, 5]thieno[2,3-d]thiazoles were synthesized by reduction of bis(3,3′-nitro-2,2′-thienyl) and bis(2,2′-nitrobenzo[b]thien-3,3′-yl) disulfides, respectively, with sodium hydrosulfite or sodium sulfide in the presence of carbon disulfide. 相似文献
14.
V. L. Savel'ev T. G. Afanas'eva S. M. Klyuev V. A. Zagorevskii 《Chemistry of Heterocyclic Compounds》1980,16(4):363-367
By the condensation of 3,4-diaminothiocoumarins containing primary or secondary amino groups in position 4, with formic and acetic acids (or acetic anhydrides), a number of 1H-[1]benzothiopyrano[3,4-d]imidazol-4-ones and their 2-methyl derivatives have been synthesized; the latter have also been obtained from the corresponding 3-monoacetylamino-4-aminothiocoumarins. By the acetylation of 3-4-diaminothiocoumarins with tertiary amino groups in positions 4 their 3-diacetyl derivative has been obtained, and these, under the action of bases, have been converted into 3-N-acetyl derivatives. The structures of the compounds synthesized have been confirmed by IR, PMR, and mass spectroscopy.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 479–483, April, 1980. 相似文献
15.
A. V. Komkov B. I. Ugrak V. S. Bogdanov V. A. Dorokhov 《Russian Chemical Bulletin》1994,43(8):1392-1397
New methods for annelation of a pyridine ring to a pyrimidine ring were suggested. Substituted 8H-pyrido[2,3-d]pyrimidin-5-ones (8a-f) were synthesized by the interaction of 2,6-disubstituted 4-amino-5-acetylpyrimidines (1–4) with formamide or acetamide acetals followed by cyclization under the action of sodium methoxide in methanol. 2,4-Disubstituted 7-phenyl-8H-pyrido[2,3-d]pyrimidin-5-ones (11a-c) were prepared by the reaction of 2,6-disubstituted 5-acetyl-4-benzoylaminopyrimidines (10a-c) with MeONa in boiling BuOH.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1469–1474, August, 1994. 相似文献
16.
Summary The reaction of 3,4-methylenedioxycinnamic acid (1) with thionyl chloride resulted in the formation of 7-chlorothieno[2,3-f]-1,3-benzodioxole-6-carbonyl chloride (2) and cinnamoyl chloride (3). Subsequent reaction of the former withp-substituted anilines led to the formation of 7-chloro-N-(p-substituted phenyl)-thieno[2,3-f]-1,3-benzodioxole-6-carboxamides (4a–c) which on photocyclization afforded 2-substituted [1,3]dioxolo[5,6][1]benzothieno[2,3-c]quinolin-6(5H)-ones (5a–c) in fairly good yields and high purity. The structures have been confirmed by IR,1H NMR, and analytical methods.Accepted for presentation at the Hong Kong International Symposium on Heterocyclic Chemistry (August 13–16, 1995) 相似文献
17.
5-Hydroxy-7-alkyl-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonitriles (VIIb-d) and 5-hydroxy-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid, ethyl ester (VIIa) were prepared from 5-carbethoxy-4-chloro-2-phenylpyrimidine (IV) via 4-[(cyanomethyl)alkylamino[-2-phenyl-5-pyrimidinecarboxylic acid, ethyl esters (Vb-d) and 4-[(carboxymethyl)amino]-2-phenyl-5-pyrimidinecarboxylic acid, diethyl ester (Va), respectively. The hydroxy group of the pyrrolo-[2,3-d]pyrimidines could be methylated, acetylated and tosylated. Hydrolysis of 5-methoxy-7-methyl-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonitrile (IX) afforded the corresponding amide (X). 相似文献
18.
A convenient and regioselective synthesis of a new heterocycle, 5-phenyl-1H or 3H-imidazo[4,5-c][1,8]-naphthyridin-4(5H)-one 1-a or 1-b , is described. Methyl 2-anilinonicotinate 15 was transformed into the valuable intermediate, N-phenyl-3-azaisatoic anhydride 4 using trichloromethyl chloroformate (TCF). Treatment of 4 with the anion of ethyl nitroacetate gave 4-hydroxy-3-nitro-1-phenyl-1,8-naphthyridin-4(5H)-one 3 . Compound 3 was chlorinated, aminated, reduced, and cyclized to afford 5-phenylimidazo[4,5-c][1,8]naphthyridin-4(5H)-one 1 . Regioselective substitution at the 1 or 3-position in the imidazole moiety of 1 was achieved by minor changes of the above scheme. 相似文献
19.
Summary. Ethyl [4-oxo-3-(2-oxo-2-arylethyl)thiazolidin-2-ylidene]acetates and [4-oxo-3-(2-oxo-2-arylethyl)thiazolidin-2-ylidene]acetonitriles
were shown to react with substituted benzaldehydes at the endocyclic methylene group leading to the corresponding 5-arylmethylidene
derivatives. Their treatment with DMF · POCl3 complex yielded 3-oxo-5-aroyl-2-arylmethylidene-2,3-dihydropyrrolo[2,1-b]thiazole-7-carboxylic acids ethyl esters and -7-carbonitriles. The structures of the pyrrolothiazoles were confirmed by an
X-ray crystallographic study, which indicated the (Z)-configuration at the arylmethylidene moiety. 相似文献
20.
Tetsuro Shimo Hidemi Minamishin Kenichi Somekawa 《Journal of heterocyclic chemistry》1997,34(2):533-536
Dehydrochlorination of chlorinated 5-hydroxy-2-oxabicyclo[3.2.0]heptan-4-ones, 3a-c, which were obtained from the photo[2+2]cycloadditions between 4-hydroxy-3(2H)-furanone 1 and chloroethylenes, with triethylamine gave 2-ethenyl-3(2H)-furanones 4a,b or 2-(2-cyanoethyl)-3(2H)-furanone 4c. 2-Oxa-bicyclo[3.2.0]hept-6-en-4-ones 7 being [2+2]cycloadducts between 1 and acetylenes gave 2,3-dihydro-3-oxooxepin derivatives 8 by electrocyclic rearrangement. 相似文献