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1.
The synthesis of the two remaining isomeric monothieno-analogues of phenanthridine N-oxide, thieno-[3,2-c]quinoline N-oxide and thieno[3,2-c]isoquinoline N-oxide, is described. The 1H and 13C nmr spectra of all six isomeric thieno-fused quinoline and isoquinoline N-oxides are discussed. 相似文献
2.
F. I. Zubkov V. P. Zaitsev A. S. Peregudov N. M. Mikhailova A. V. Varlamov 《Russian Chemical Bulletin》2007,56(5):1063-1079
A procedure was developed for the synthesis of hydrogenated furyl-substituted furo[3,2-c]quinolines, pyrano[3,2-c]quinolines, and 4-ethoxy-and 4-(2-oxopyrrolidin-1-yl)quinolines. The reactions of these compounds with acryloyl chloride
and maleic anhydride produce epoxyisoindolo[2,1-a]quinoline derivatives through successive acylation at the quinoline nitrogen atom and intramolecular exo-[4+2]-cycloaddition at the furan moiety.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1023–1038, May, 2007. 相似文献
3.
S. C. Perricone Edward F. Elslager Donald F. Worth 《Journal of heterocyclic chemistry》1970,7(1):135-138
The boron trifluoride catalyzed 1,4-addition of 2,3-dihydro-5-methylfuran to N-(p-methoxy-benzylidene)-1,4-benzodioxan-6-amine (II) gave 2 pairs of epimers, 2,3,3a,4,5,8,9,11b-octahydro-4-(p-methoxyphenyl)-11b-methyl-p-dioxino[2,3-g]furo[3,2-c]quinoline (IIIa and b) and 2,3,7,8,8a,9.10,1la-octahydro-8-(p-methoxyphenyl)-11a-methyl-p-dioxino[2,3-f]furo[3,2-c]quinoline (IVa and b). When N-(p-methoxybenzylidene)-3,4-methylenedioxyaniline (V) was condensed with 2,3-dihydro-5-methylfuran in an analogous manner, a mixture of 2 epimers of 2,3,3a,4,5,10b-hexahydro-4-(p-methoxyphenyl)-10b-methyl[1,3]dioxolo[4,5-g]furo[3,2-c]quinoline (VIa and b) was isolated. Treatment of this mixture with sulfur afforded 6-(p-methoxyphenyl)-8-methyl-1,3-dioxolo[4,5-g]quinoline-7-ethanol (VIII). Structural assignments for all of the products were made from NMR spectra. None of the compounds possessed appreciable biological activity. 相似文献
4.
S. C. Perricone Donald F. Worth Edward F. Elslager 《Journal of heterocyclic chemistry》1970,7(3):537-542
The 1,4-cycloaddition of 2,3-dihydro-5-methylfuran (II) to 1-acetyl-1,2,3,4-te trahydro-6-[(p-hydroxybenzylidene)amino]quinoline (VIII) in the presence of boron trifluoride gave two pairs of epimers, namely dl-10-acetyl-2,3,3a,4,5,7,8,9,10,11b-decahydro-4-(p-hydroxyphenyl)-11b-methylfuro[3,2-c]pyrido[2,3-g]quinoline (IXa and b) and dl-8-acetyl-2,3,3a,4,5,8,9,10,11,-11c-decahydro-4-(p-hydroxyphenyl)-11c-methylfuro[2,3-a][4,7]phenanthroline (Xa and b). dl-9-Acetyl-3,3a,4,5,7,8,9,10b-octahydro-4-(p-hydroxyphenyl)-10b-methyl-2H-furo[3,2-c] pyrrolo-[2,3-g]quinoline (XIIIa) was the predominant product isolated from the reaction of II with 1-acetyl-5-[p-(hydroxybenzylidene)amino]indoline (XII). When 1-acetyl-6-[(p-hydroxybenzylidene)amino]indoline (XVI) was treated with 2,3-dihydro-5-methylfuran (II), two epimers of dl-7-acetyl-3,3a,4,5,7,8,9,10b-octahydro-4-(p-hydroxyphenyl)-10b-methyl-2H-furo[3,2-c]pyrrolo[3,2-g]quinoline (XVIIa and b) were obtained. dl-2,3,3a,4,5,6b,8,9,9a,10,11,12b-Dodecahydro-4,10-bis(p-methoxyphenyl)-6b,12b-dimethylfuro[3,2-c]furo[2′,3′:4,5]pyrido[2,3-g]quinoline (XX) was formed when 2,3-dihydro-5-methylfuran was allowed to react with N,N'-bis(p-methoxybenzylidene)-p-phenylcnediamine (XIX). Structure assignments were made from NMR spectra. None of the compounds exhibited appreciable biological activity. 相似文献
5.
Donald F. Worth S. C. Perricone Edward F. Elslager 《Journal of heterocyclic chemistry》1970,7(6):1353-1356
The boron trifluoride catalyzed 1,4-addition of 2,3-dihydro-5-methylfuran to N-(p-methoxybenzylidene)-5-indanamine (VI) gave 2 pairs of epimers, dl-3,3a,4,5,7,8,9,10b-octahydro-4-(p-methoxyphenyl)-10b-methyl-2H-cyclopenta[g]furo[3,2-c]quinoline (VIIa and b) and dl-3,3a, 4,-5,8,9,10,10c-octahydro-4-(p-methoxyphenyl)-10c-methyl-2H-cyclopenta[f]furo[3,2-c]quinoline (VIIIa and b). When 4-(benzylideneamino)-1-naphthol (IXa) was condensed with 2,3-dihydro-5-methylfuran in an analogous manner, a mixture of two isomers of dl-1,2,2a,3,4,5a-hexahydro-5a-methyl-2-phenylbenzo[h]furo[3,2-c]quinolin-7-ol [Xa and b (R ? H)] was obtained. Likewise, 4-[(p-hydroxybenzylidene)amino]-1-naphthol (IXb) and 4-(p-methoxybenzylidene)amino]-1-naphthol (IXc) gave a mixture of two isomers of dl-1,2,2a,3,4,5a-hexahydro-2-(p-hydroxyphenyl)-5a-methylbenzo[h]furo[3,2-c]quinolin-7-ol [Xa and b (R ? OH)] and dl-1,2,2a,3,4,5a-hexahydro-2-(p-methoxyphenyl)-5a-methylbenzo [h]furo[3,2-c]quinolin-7-ol [Xa and b (R ? OCH3)], respectively. The condensation of N-(p-methoxybenzylidene)-5-acenaphthenamine (XI) with 2,3-dihydro-5-methylfuran afforded a mixture of two isomers of dl-2,3,3a,4,5,9,10,-11b-octahydro-4-(p-methoxyphenyl)-11b-methylfuro[3,2-c]indeno[1,7-gh]quinoline (XIIa and b). Structural assignments for all of the products were made from NMR spectra. None of these compounds possessed appreciable biological activity. 相似文献
6.
Evelina Colacino 《Tetrahedron letters》2008,49(33):4953-4955
A new and high yielding approach for the synthesis of a novel pyrrolo-[3,2-c]quinoline N-oxide is described. The key step consisted in the palladium-catalyzed reductive cyclization of an uncommon 3-ketopyrrole derivative of o-nitrobenzaldehyde, obtained in a straightforward manner through an aza-Baylis-Hillman/ring closing metathesis/aromatization reaction. A deoxygenation reaction of this novel pyrrolo-[3,2-c]quinoline N-oxide afforded a new substituted pyrrolo-[3,2-c]quinoline analogue. 相似文献
7.
Photocyclization of 3-chloro-N-phenylbenzo[b]thiophene-2-carboxamide 10 afforded [1]benzothieno[2,3-c]-quinolin-6(5H)-one 11 which was chlorinated to 6-chloro[1]benzothieno[2,3-c]quinoline 12 followed by dechlorination to give [1]benzothieno[2,3-c]quinoline 5 . A series of 6-substituted alkoxy and thioalkoxy[1]benzothieno[2,3-c]quinoline derivatives were prepared along with the N-methyl quaternary salt 13 of 5 . 6-Chloro[1]-benzothieno[2,3-c]quinoline 12 was converted into 6-hydrazino[1]benzothieno[2,3-c]quinoline 23 which upon treatment with formic acid yielded [1]benzothieno[2,3-c][1,2,4]triazolo[4,3-a]quinoline 6 . Treatment of 23 with nitrous acid resulted in [1]benzothieno[2,3-c]tetrazolo[1,5-a]quinoline 7 . Compounds 6 and 7 are novel heterocyclic ring systems. 相似文献
8.
Synthesis of novel thiazoloindolo[3,2-c]quinoline and 8-substituted-11H-indolo[3,2-c]quinolines was performed via Graebe-Ullmann thermal cyclization from appropriated N-arylated benzotriazoles. 7H-4,7-Diaza-benzo[de]anthracene, a by-product reaction structurally closed to pyridoacridine skeleton was also identified. 相似文献
9.
4-Methylfuro[3′,2′:5,6]benzofuro[3,2-c]pyridine ( 3 ) was synthetized from 2-acetylfuro[3,2-f]benzo[b]furan ( 4 ) or from 2-acetyl-5,6-dihydrofuro[3,2-f]benzo[b]furan ( 10 ). The key step involves a rearrangement-cyclization of azides 6 and 12 to form 4-methylfuro[3′,2′:5,6]benzofuro[3,2-c]pyridin-1(2H) one ( 7 ) and 8,9-dihydro-4-methylfuro[3′,2′:5,6]benzofuro[3,2c]pyridin-1(2H)-one ( 13 ). Introduction of an aminoalkyl chain on carbon 1 was effected by substitution of 1-chloro-4-methylfuro[3′,2′:5,6]benzofuro[3,2-c]pyridine ( 8 ). 相似文献
10.
3-Amino-4-hydroxy-6-phenylpyrano[3,2-c]quinoline-2,5(6H)-dione was produced by a smooth reduction of its nitro precursor. Reaction of this 3-amino-4-hydroxypyranoquinoline derivative with different electrophiles, leading to a variety of oxazolo and oxazinopyrano[3,2-c]quinoline derivatives, was described. The structure of the new products was elucidated via elemental analysis, IR, 1H NMR, 13C NMR, and mass spectra. Also, screening the antitumor activity of new compounds against two human cell lines (HepG-2 and HCT-116) was carried out. Some new products showed significant antitumor activities. 相似文献
11.
John W. Mcfarland William A. Essary Lale Cilenti William Cozart Philip E. Mcfarland 《Journal of heterocyclic chemistry》1975,12(4):705-707
Furo[3,2-c] pyridine (I) was nitrated to give 2-nitrofuro[3,2-c]pyridine (II). Bromination and chlorination of I gave, respectively, 2,3-dibromo-2,3-dihydrofuro[3,2-c]pyridine (III) and 2,3-dichloro-2,3-dihydrofuro[3,2-c]pyridine (IV). Oxidation of I with hydrogen peroxide afforded furo[3,2-c]pyridine 5-oxide (V) which was converted to I by phosphorus trichloride and to 4-chlorofuro[3,2-c]pyridine (VI) by phosphorus oxychloride. 相似文献
12.
9,10-Dimethoxy-1,2,3,4,12,13-hexahydro-1-oxoquino[1,2-c]quinazolinium perchlorate, 1,2,3,4,13,24-hexahydro-1-oxo[1,3]dioxolo[4,5-g]quino[1,2-c]quinazolinium perchlorate, 6-methyl-2,3,9,10-tetramethoxyquino-[1,2-c]quinazolinium perchlorate and 2,3-dimethoxy-13-methyl[1,3]dioxolo[4′,5′:6,7]quino[1,2-c]quinazolinium perchlorate were synthesized as analogs of the potent antitumor benzo[c]phenanthridine alkaloids nitidine and fagaronine. The related 2,3,8,9-tetramethoxyindazolo[2,3-a]quinoline and 2,3-dimethoxy[1,3]dioxolo-[4,5-g]indazolo[2,3-a]quinoline were also synthesized. Further, the novel formation of 6,7-dimethoxy-2-(2-ethylamino-4,5-dimethoxyphenyl)quinoline via reductive alkylation with Raney nickel in refluxing ethanol is also reported. 相似文献
13.
M. Robba M. Cugnon de Sevricourt J. M. Lecomte 《Journal of heterocyclic chemistry》1975,12(3):525-527
The cyclization reactions of the 4-hydrazinothieno[2,3-d]pyrimidines give s-triazolo[1,2-c]-thieno[3,2-e]pyrimidines and tetrazolo[1,5-c]thieno[3,2-e]pyrimidines. 相似文献
14.
Dattatray G. HinganeRadhika S. Kusurkar 《Tetrahedron letters》2011,52(28):3686-3688
An efficient and short route is established for biologically active 11H-indolo[3,2-c]quinoline 1, naturally occurring antiplasmodial isocryptolepine 2 and 5-methyl-11H-indolo[3,2-c]quinoline-5-inium iodide 3 using intramolecular thermal electrocyclization strategy. 相似文献
15.
The synthesis of three novel polycyclic heterocyclic ring systems are reported via photocyclization. The specific final products in these ring systems are: phenanthro[9′,10′:4,5]thieno[2,3-c]quinoline ( 13 ), benzo[h]-phenanthro[9′,10′:4,5]thieno[2,3-c]quinoline ( 14 ), and benzo[f]phenanthro[9′,10′:4,5]thieno[2,3-c]quinoline ( 15 ). 相似文献
16.
Johan Malm Anna-Britta Hrnfeldt Salo Gronowitz 《Journal of heterocyclic chemistry》1994,31(2):521-525
Thieno[2,3-c]-1,5-naphthyridine ( 3 ), thieno[2,3-c]1,5-naphthyridine 5-oxide ( 7 ), thieno[3,2-c]-1,5-naphthyridine ( 5 ) and thieno[3,2-c]-1,5-naphthyridine 5-oxide ( 9 ) could conveniently be brominated at room temperature using dibromoisocyanuric acid in fuming sulfuric acid. Bromination occurred in good to moderate yields at the β position in the thiophene ring. Thieno[2,3-c]-1,5-naphthyridine 9-oxide ( 12 ) and thieno[3,2-c]-1,5-naphthyridine 9-oxide ( 13 ) also gave substitution in the thiophene ring at 95°. It was also found that 12 was deoxygenated under these reaction conditions. Direct oxidation of the brominated thieno[c]naphthyridines with m-chloroperbenzoic acid gave the 5-oxides in high yield. 相似文献
17.
Emile Bisagni Alain Civier Jean-Pierre Marquet 《Journal of heterocyclic chemistry》1975,12(3):461-465
Treatment of 4-hydroxy-6-methylpyran-2-one with chloracetalhyde in basic aqueous medium gave 6-methylfuro[3,2-c]pyran-4-one. This compound reacted with ammonium hydroxide and some primary amines to form the corresponding N-substituted furo[3,2-c]pyrid-4-ones which may also be obtained from 4-hydroxy-α-pyridones. Furo[3,2-c]pyran-4-one was acylated at the 2 position and 4-chloro-6-methylfuro[3,2-c]pyridine easily gave 4-substituted derivatives by displacement of the halogen atom. 相似文献
18.
Shivayogi P. Hiremath Ananda R. Saundane B. H. M. Mruthyunjayaswamy 《Journal of heterocyclic chemistry》1993,30(3):603-609
The synthesis of 8-substituted and unsubstituted 6H,11H-indolo[3,2-c]isoquinolin-5-ones/thiones 3a-c and 4a-c and their derivatives viz, ethyl (8-substituted-6H,11H-indolo[3,2-c]isoquinolin-5-on-6-yl)acetates 5a-c , (8-substituted-6H,11H-indolo[3,2-c]isoquinolin-5-on-6-yl)acetyl hydrazides 6a-c , 3,5-disubstituted-pyrazoles 7a-c and 8a-c , 3-substituted-pyrazol-5-ones 9a-c and 5-(8-substituted-6H,11H-indolo[3,2-c]isoquinolin-5-on-6-yl)methyl-1,3,4-oxadiazole-2-thiones 10a-c , also ethyl (8-substituted-11H-indolo[3,2-c]isoquinolin-5-ylthio)ace-tates 11a-c , (8-substituted-11Hindolo[3,2-c]isoquinolin-5-ylthio)acetyl hydrazides 12a-c , 3,5-disubstituted-pyrazoles 13a-c and 14a-c , 3-substituted-pyrazol-5-ones 15a-c and 5-(8-substituted-11H-indolo[3,2-c]isoquin-olin-5-yl)thiomethyl-1,3,4-oxadiazole-2-thiones 16a-c is described. 相似文献
19.
4-Chloro-2-methylfuro[2,3-c]quinoline (IV) was synthesized from ethyl 3-(2-nitrophenyl)-5-methyl-2-furoate and IV was allowed to react with some nucleophiles to afford the corresponding 4-substituted 2-methylfuro-[2,3-c]quinoline derivatives, respectively. On treatment of IV with potassium azide in dimethylsulfoxide, 2-methylfuro[2,3-c]tetrazolo[1,5-a]quinoline was formed path azido-tetrazolo isomerization. 2-Methylfuro-[2,3-c]quinoline was prepared by the reduction of IV. 相似文献
20.
Salo Gronowitz Curt Roos Elina Sandberg Sergio Clementi 《Journal of heterocyclic chemistry》1977,14(5):893-897
Deuteriodeprotonation of some substituted 4,5-borazarothieno[2,3-c]pyridines (I) and 7,6-borazarothieno[3,2-c]pyridines (II) has been studied by the nmr technique. Exchange occurred predominantly in the 3-position, and the effect of methyl substitution on rate is discussed. The rates of exchange in some derivatives of I and II were compared with those of the isoelectronic thieno[2,3-c]pyridines (III) and thieno[3,2-c]pyridines (IV). Similar rates were obtained, confirming the aromatic nature of I and II. The deuteriodeprotonation of 4-methyl-4,5-borazaro-thieno[2,3-c]pyridine (Ie), 7-methyl-7,6-borazarothieno[3,2-c]pyridine (IIe), 4-methylthieno-[2,3-c]pyridine (IIIe), and 7-methylthieno[3,2-c]pyridine (IVe) were measured at different concentrations of deuteriosulfuric acid and different temperatures, showing that the protonated heterocycles are substrates in the deuteriodeprotonation reaction. Standard rates at p0 H and 100° were calculated for these systems. 相似文献