共查询到20条相似文献,搜索用时 46 毫秒
1.
Praziquantel, 2-cyclohexylcarbonyl-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one, is a novel antiparasitic drug possessing one chiral center.[1] In the study of structure-activity relationship of praziquantel we were interested in its structural modification. 1-Benzyl Reissert compound of isoquinoline is required as starting materials for the synthesis of praziquantel analogues with modified chiral centers. On the other hand, we want to know what could be obtained when 1-benzyl Reissert compounds were exposed to high pressure catalytic hydrogenation. In this paper we report the results in the hydrogenation of 1-benzyl Reissert compound. 相似文献
2.
O. V. Khilya T. A. Volovnenko Yu. M. Volovenko 《Chemistry of Heterocyclic Compounds》2006,42(10):1311-1324
The reaction of 4-oxo-3,4-dihydroquinazolyl-and benzimidazolylacetonitriles with 2-chloro-2-quinolinecarbaldehydes and 1-aryl-5-chloro-3-methyl-1H-pyrazole-4-carbaldehydes
gave the corresponding 3-(2-chloro-3-quinolyl)-2-(4-oxo-3,4-dihydro-2-quinazolyl)-2-propenenitriles and 3-(1-aryl-5-chloro-3-methyl-1H-4-pyrazolyl)-2-hetaryl-2-propenenitriles.
Intramolecular cyclization of these compounds gives 15-oxo-15H-benzo[6,7][1,8]naphthyridino[2,1-b]quinazoline-6-carbonitriles,
1-aryl-3-methyl-11-oxo-1,11-dihydropyrazolo[4′,3′:5,6]pyrido[2,1-b]quinazoline-5-carbonitriles, and 1-aryl-3-methyl-1H-benzo[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyridine-5-carbonitriles. 相似文献
3.
M. M. Kamel M. M. Anwar A. M. Soliman H. F. Abdel-Hamid 《Research on Chemical Intermediates》2013,39(7):3417-3426
Praziquantel, 2-(cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one, was used as the parent starting material to synthesize a new series of praziquantel-3-arylidene derivatives 1a–c and praziquantel–Mannich bases 2a–d, hoping to obtain new antischistosomal compounds of more activity and lower adverse effects. The antischistosomal activity of the newly synthesized compounds was evaluated using in vitro Schistosoma mansoni worm killing tests. Both compounds 2c and 2d exhibited significant in vitro antischistosomal activity and may offer promising use as an antischistosomal drug either alone or in combination with praziquantel. 相似文献
4.
Giuseppe Daidone Salvatore Plescia Jole Fabra 《Journal of heterocyclic chemistry》1980,17(7):1409-1411
Thermal decomposition of the diazonium sulfate derived from N-methyl-(1-phenyl-3-methylpyrazol-5-yl)-2-aminobenzamide afforded products formulated as 1-phenyl-3-methyl[2]benzopyrano[4,3-c]pyrazol-5-one (yield 10%), 1,4-dimethyl-3-phenylpyrazolo[3,4-c]isoquinolin-5-one (yield 10%), N-methyl-(1-phenyl-3-methylpyrazol-5-yl)-2-hydroxybenzamide (yield 8%) and 4′-hydroxy-2,3′-dimethyl-1′-phenylspiro[isoindoline-1,5′-[2]-pyrazolin]-3-one (yield 20%). Decomposition of the diazonium sulfate derived from N-methyl-(1,3-diphenylpyrazol-5-yl)-2-aminobenzamide gave products formulated as 7,9-dimethyldibenzo[e,g]pyrazolo[1,5-a][1,3]-diazocin-10-(9H)one (yield 8%), 4-methyl-1,3-diphenylpyrazolo[3,4-c]isoquinolin-5-one (yield 7%) and 4′-hydroxy-2-methyl-1′,3′-diphenylspiro[isoindoline-1,5′-[2]pyrazolin]3-one (yield 10%). The spiro compounds 6a,b underwent thermal and acid-catalysed conversion into the hitherto unknown 2-benzopyrano[4,3-c]pyrazole ring system 7a,b in good yield. Analytical and spectral data are presented which supported the structures proposed. 相似文献
5.
A one-pot procedure was developed for the synthesis of 3-isothiocyanatopropionaldehyde and 3-isothiocyanatobutyraldehyde diethyl acetals from the corresponding α,β-unsaturated aldehydes. Reactions of 1,1-diethoxy-3-isothiocyanatobutane with aliphatic amines and hydrazines gave, respectively, substituted thioureas and thiosemicarbazides which underwent acid-catalyzed cyclization to form 6-ethoxytetrahydropyrimidine-2(1H)-thiones, 9,10-dimethoxy-2-methyl-1,2,3,6,7,11b-hexahydro-4H-pyrimido[6,1-a]isoquinoline-4-thiones, and 2-methyl-2,3,6,7,12,12b-hexahydropyrimido[1′,6′:1,2]pyrido[3,4-b]indole-4(1H)-thione. 相似文献
6.
First total syntheses of the 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines annoretine and litebamine
《Tetrahedron》2003,59(40):8057-8065
We describe here the first total synthesis of the two natural 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines, annoretine and litebamine, from [2-(2-styrylphenyl)ethyl]methylcarbamic acid ethyl esters. The key steps were the Bischler-Napieralski cyclization to form the isoquinoline unit and photocyclization of the resulting 2-methyl-5-styryl-3,4-dihydro-2H-isoquinolin-1-ones to 2-methyl-3,4-dihydro-2H-naphtho[2,1-f]isoquinolin-1-ones. 相似文献
7.
O. V. Gulyakevich P. V. Kurman A. S. Lyakhov A. L. Mikhal’chuk 《Chemistry of Heterocyclic Compounds》2006,42(1):70-76
Treatment of 3,4-dihydroisoquinolines with triacetylmethane in refluxing alcohol for 2-3 h gave 3-acetyl-4-methylpyrido[2,1-a]isoquinolin-2-ones.
Their basic physicochemical properties have been studied.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 77–85, January, 2006. 相似文献
8.
Cycloaddition in condensed isoindoles 1. Preparation of 2-aryl-3-methyl-4-oxo-3,4-dihydroquinazoline
Z. V. Voitenko V. P. Samoilenko V. A. Kovtunenko V. Yu. Gurkevich A. K. Tyltin M. V. Shcherbakov O. V. Shishkin 《Chemistry of Heterocyclic Compounds》1999,35(5):600-607
Reaction of 6-methyl-5,6-dihydroisoindolo[2,1-a]quinazolin-5-one with maleimide derivatives has been studied under conditions
of thermodynamic control. X-ray diffraction structural analysis showed that the reaction products are 2{2-[(E)-1-R-2,5-dioxopyrrolidinidenemethyl]phenyl}-3-methyl-4-oxo-3,4-dihydroquinazolines.
These products are supposed to be formed by rearrangement of the corresponding Diels-Alder adducts formed involving the isoindole
part of the molecule.
Taras Shevchenko Kiev University, 252033 Kiev, Ukraine; Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp.
669–677, May, 1999. 相似文献
9.
S. Y. S. Beheshtiha R. Hekmatshoar F. Soltani 《Phosphorus, sulfur, and silicon and the related elements》2013,188(9):1723-1729
A series of new 1,8-naphthylimide and 4-(thio)-7H-benzimidazo[2,1-a]benz[d,e]isoquinolin-7-one derivatives has been synthesized, and the UV/Vis absorptioin characteristics discussed. Substituents' effect on the UV/Vis absorption characteristics have been investigated. 相似文献
10.
In the reaction of 4a-methyl-2,3,4,4a-tetrahydro-1H-carbazole and its 6-methyl- and 6-bromosubstituted derivatives with 2-chloroacetamide
respectively by 9-carbamoylmethyl-4a-methyl-2,3,4,4a-tetrahydro-1H-carbazolium chlorides are formed, which can be cyclized
into 5,6,7,7a-tetrahydro-1H, 4H-imidazo[2,1-k]-carbazol-2(3H)-one derivatives. Reaction of 4a-methyl-2,3,4,4a-tetrahydro-1H-carbazole
hydrochloride with acrylamide gives 8a-methyl-1,2,6,7,8,8a-hexahydro-5H-pyrimido[2,1-k]carbazol-3(4H)-one. 7a, 12-Dimethyl-3,4,4a,5,6,7,7a,12-octahydropyrido[3,2-j]carbazol-2(1H)-one
was synthesized by the reaction of 4a,9-dimethyl-2,3,4,4a-tetrahydro-9H-carbazole with acrylamide.
Department of Organic Chemistry, Kaunas University of Technology, Kaunas LT-3028, Lithuania; Published in Khimiya Geterotsiklicheskikh
Soedinenii, No. 5, pp. 645–648, May 1999. 相似文献
11.
A. A. Bogolyubov N. B. Chernysheva V. V. Semenov 《Chemistry of Heterocyclic Compounds》2004,40(9):1124-1130
4-(Bromomethylene)-5,5-dimethyl-1,3-dioxolan-2-one was obtained on the basis of the readily obtainable 4-methylene-5,5-dimethyl-1,3-dioxolan-2-one. It forms 2-imidazo[1,2-a]pyridin-2-yl-2-propanol with 2-aminopyridine, 11a-hydroxy-1,1-dimethyl-3-oxo-1,5,11,11a-tetrahydro[1,3]oxazolo[3,4-a]pyrido[1,2-d]-10-pyrazinium bromide with 2-(aminomethyl)pyridine, and the corresponding derivative of 4-hydroxyoxazolidin-2-one with 2-(3,4-dimethoxyphenyl)ethylamine. The last product was converted by intramolecular amidoalkylation without isolation into 10b-(bromomethyl)-8,9-dimethoxy-1,1-dimethyl-1,5,6,10b-tetrahydro[1,3]oxazolo[3,4-a]isoquinolin-3-one. 相似文献
12.
The reaction of 2-chloro-4-(methylsulfonyl)benzoyl chloride ( 5 ) with 1-methyl-1H-2,1-benzothiazin-4-(3H)-one 2,2-dioxide ( 4 ) gave the O-benzoyl compound, 1-methyl-2,2-dioxido-1H-2,1-benzothiazin-4-yl 2-chloro-4-(methylsulfonyl)benzoate ( 6 ), which rearranged to give the C-benzoyl isomer, [2-chloro-4-(methylsulfonyl)phenyl] (4-hydroxy-1-mefhyl-2,2-dioxido-1H-2,1-benzothiazin-3-yl)methanone ( 7 ). The O-cinnamoyl compound 13 that resulted from the addition of 2,4-dichlorocinnamoyl chloride ( 11 ) to compound 4 rearranged to give the C-cinnamoyl compound, 3-(2,4-dichlorophenyl)-1-(4-hydroxy-1-methyl-2,2-dioxido-1H-2,1-benzothiazin-3yl)-2-propen-1-one ( 15 ). On the other hand, 1-methyl-2,2-dioxido-1H-2,1-benzothiazin-4-yl 3-phenyl-2-propenoate ( 19 ) (from cinnamoyl chloride ( 17 ) and compound 4 ) rearranged to give 2,3-dihydro-6-methyl-2-phenyl-4H,6H-pyrano[3,2-c][2,1]benzothiazin-4-one 5,5-dioxide ( 21 ), an example of a hitherto unknown ring system. Additional examples of this novel heterocycle were prepared from 1-methyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide ( 23 ) and 1-methyl-1H-thieno[3,2-c][1,2]thiazin-4(3H)-one 2,2-dioxide ( 8 ). 相似文献
13.
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
14.
The condensation of 1-acyl-2-(morpholin-4-yl)cycloalkenes with 3-amino-1-phenyl-1H-pyrazol-5(4H)-ones gave the corresponding 2,3,6,7,8,9-hexahydropyrazolo[3,4-c]isoquinoline and 3,6,7,8,9,10-hexahydrocyclohepta[ d]pyrazolo[3,4-b]pyridine derivatives. Alkylation of 2,3,6,7,8,9-hexahydropyrazolo[3,4-c]-isoquinolines with alkyl halides occurred at the nitrogen atom in the 3-position. The structure of 7-methyl-2,5-diphenyl-2,3,6,7,8,9-hexahydro-1H-pyrazolo[3,4-c]isoquinolin-1-one was proved by X-ray analysis. 相似文献
15.
V. A. Dorokhov M. F. Gordeev Z. K. Dem'yanets L. G. Vorontsova M. G. Kurella V. I. Andrianov O. A. Rekhlov 《Russian Chemical Bulletin》1991,40(11):2262-2266
3-Phenyl-5-methyl(phenyl)-1H,3H-pyrimido[4,5:4,5]pyrimido[1,2-a]benzimi-dazole-2,4-diones were obtained by the cyclization of N-phenyl-N-[3-ethoxycar-bonyl-4-methyl(phenyl)pyrimido [1,2-a]benzimidazol-2-yl]ureas by the action of potassium carbonate. 2-Methyl-5-phenyl-1H-pyrimido[4,5:4,5]pyrimido[1,2-a]benzimidazol-4-one was obtained by the reaction of N-3-ethoxycarbonyl-4-phenylpyrimido[1,2-a]benzimidazol-2-yl]-N,N-dimethylacetamidine with ammonium acetate in ethanol. The synthesized compounds are members of a new heterocyclic system. The molecular and crystal structure of the solvate of 3-phenyl-5-methyl-1H,3H-pyrimido[4,5:4,5] pyrimido[1,2-a]benzimidazole-2,4-dione with two molecules of DMF was studied by x-ray crystallographic analysis.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2587–2592, November, 1991. 相似文献
16.
L. M. Potikha A. R. Turelyk V. A. Kovtunenko A. V. Turov G. V. Palamarchuk R. I. Zubatyuk O. V. Shishkin 《Chemistry of Heterocyclic Compounds》2010,46(6):742-753
(Z)-4-Bromo-1,3-di(2-thienyl)-2-buten-1-one was obtained by the bromination of 1,3-di(2-thienyl)-2-buten-1-one by NBS in anhydrous
CCl4. The starting butanone was obtained by the condensation of 1-(2-thienyl)-1-ethanone by the action of SOCl2. The reaction of (Z)-4-bromo-1,3-di(2-thienyl)-2-buten-1-one with tertiary amines such as Et3N, pyridine, 1-alkyl-1,3-diazole, 1-alkylbenzimidazole, and 1-alkyl-1,2,4-triazole leads to quaternary salts. The azolium
salts cyclize by the action of base to give di(2-thienyl)azolo[a]pyridinium derivatives. 3-Methyl-6,8-di(2-thienyl)[1,3]thiazolo[3,2-a]pyridin-4-ium
and 2,4-di(2-thienyl)pyrido[2,1-b]benzothiazol-10-ium bromides were obtained by the same procedure but without separating
the intermediate quaternary salts. 相似文献
17.
A. K. Fogla Vandana Ankodia Praveen Kumar Sharma M. Kumar 《Research on Chemical Intermediates》2009,35(1):35-41
N-bridged heterocycles, 2-methyl-4H-pyrimido[2,1-b]benzothiazol-4-ones, have been synthesized in quantitative yield by the reaction of 2-aminobenzothiazoles with ethylacetoacetate
in the presence of polyphosphoric acid involving dehydrative condensation followed by cyclization. The possibility of the
formation of 4-methyl-2H-pyrimido[2,1-b]benzothiazol-2-ones has been excluded on the basis of spectral studies. 相似文献
18.
L. M. Potikha R. M. Gutsul A. S. Plaskon V. A. Kovtunenko A. A. Tolmachev 《Chemistry of Heterocyclic Compounds》2011,47(3):342-354
The reaction of 3-NHR-isoquinolin-1(2H)-ones (R = Ar) with aromatic aldehydes in the presence of Me3SiCl or in acetic acid
leads to the formation of derivatives of dibenzo[b,f][1, 8]naphthyridin-5(6H)- one and benzo[f]isoquino[3,4-b][1, 8]naphthyridine-5,9(6H,7H)-dione.
The reaction for R = Het in the presence of Me3SiCl gives derivatives of 5H-pyrido[1',2':1,2]pyrimido[4,5-c]isoquinolin-5-one,
benzo[f]isoquinoline[3,4-b][1,8]naphthyridine-5,9[6H,7H]-dione, and derivatives of new heterocyclic systems, 5H-pyrazino[1',2':1,2]pyrimido[4,5-c]isoquinolin-5-one,
5H-[1,3]thiazolo[3',2':1,2]pyrimido- [4,5-c]isoquinolin-5-one, 5-H-benzo[f]pyrazolo[3,4-b][1,8]naphthyridin-5-one, and isoquino[3,4-b]-
[1,5]naphthyridin-5(6H)-one. The effect of the structure of substituent R and nature of the substituent in the benzaldehydes
on the structure of the reaction products was studied. 相似文献
19.
Russian Journal of Organic Chemistry - 8-Aroyl-3,4-dihydro-1H-pyrrolo[2,1-a][1,4]oxazine-1,6,7-triones reacted with 3-benzylamino-5,5-dimethylcyclohex-2-en-1-one to give... 相似文献
20.
Two 1,8-naphthalimide derivatives of 7H-benzimidazo[2,1,-a]benz[de] isoquino- lin-7-one(1) and 4-bromo-7H-benzimidazo[2,1,-a]benz[de]isoquinolin-7-one(2) have been synthesized and characterized by elemental analysis, IR, 1H NMR, UV-Vis and fluorescence spectra. For the two compounds, density functional theory(DFT) calculations of the structures and natural population atomic charge analysis have been performed at the B3LYP/6-311G** level of theory. Based on Onsager reaction filed model and by using TD-DFT method at the B3LYP/6-311G** level, electron spectra of 1 and 2 with solvent effect in CHCl3 solvent have been predicted, which are in agreement with the experimental ones. Comparative studies on 1 and 2 indicate that introducing an electron-withdrawing group of Br into the 4-position of naphthalene ring in 2 does not significantly make the molecular geometry of 2 different from that of 1, but evidently changes the atomic charge redistribution, moves the positive-negative charges center and then changes the dipole moment in 2. Additionally, for compound 2, the existence of Br atom has also influenced the peak intensity and peak locations in both electron and fluorescence spectra. 相似文献