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1.
Akira Tanaka Kenichi Yakushijin Shigetaka Yoshina 《Journal of heterocyclic chemistry》1979,16(4):785-788
Methyl or ethyl 4H-furo[3,2-b]indole-2-carboxylates (Va,b) were prepared from deoxygenation of methyl or ethyl 5-(2-nitrophenyl)-2-furoates (IIIa,b) and thermolysis of methyl or ethyl 5-(2-azidophenyl)-2-furoates (VIIIa,b). 4H-Furo[3,2-b]indole-2-carboxylic acid amides (XIa-h) were obtained by the reaction of 4H-furo[3,2-b]indole-2-carboxyl chloride (X) with the appropriate amines. 相似文献
2.
The rearrangement of 2-amino-3-carbethoxy-4-ethylfuro[3,2-b]pyridinium iodide in basic solution was studied. The reaction product is 2-oxo-3-cyano-4-ethyl-4H-furo[3,2-b]pyridine which was obtained also by alkylation with ethyl iodide and sodium hydride in dimethylformamide of 2-oxo-3-cyano-3H-furo[3,2-b]-pyridine or of p-nitrophenyl-3-acetoxypyridine-2-cyanacetate. 相似文献
3.
The hydrazones derived from coumarin-6-ylhydrazine and ethyl 6-hydrazinochromone-2-carboxylate undergo facile indolization to give 3H,7H-pyrano[3,2-e]indol-7-ones (IIIb-IIIg) and ethyl 9-oxo-3H,9H-pyrano[3,2-e]indole-7-carboxylates (IVb-IVd), respectively, in good yields. Compounds IVb-IVd are derivatives of a new ring system. 相似文献
4.
S. Yu. Ryabova L. M. Alekseeva N. A. Rastorgueva E. A. Lisitsa D. M. Papakhin V. A. Parshin V. G. Granik 《Russian Chemical Bulletin》2006,55(12):2278-2284
Reactions of 3-[(N-aryl-N-chloroacetyl)amino]-2-formylindoles with substituted anilines gave 1,4-diaryl-2-oxo-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indol-4-ium chlorides and those with 4-aminopyridine yielded 4-amino-1-(1-aryl-2-oxo-2,5-dihydro-1H-pyrido[3,2-b]indol-3-yl)pyridinium chlorides. Reduction of 1,2,3,6-tetrahydrodiazepinoindol-4-ium chlorides afforded the corresponding
hexahydro derivatives. An alternative synthesis of 1-(4-nitrophenyl)-3-oxo-4-phenyl-1,2,3,4,5,6-hexahydro[1,4]diazepino[6,5-b]indole from 3-[N-(4-nitrophenyl)amino]-2-[(phenylimino)methyl]indole was developed. The method involves the following sequence of transformations:
reduction, chloroacetylation, and intramolecular alkylation.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2193–2199, December, 2006. 相似文献
5.
V. Yu. Mortikov L. A. Rodinovskaya A. E. Fedorov A. M. Shestopalov P. A. Belyakov 《Russian Chemical Bulletin》2014,63(2):443-456
Formylation of pyrazole and 2,5-dimethylpyrazole gave a number of pyrazole-containing aldehydes, which can be used to obtain chromenes, tetrahydrochromenes, 1,4-dihydropyrano[2,3-c]pyrazoles, pyrano[3,2-c]chromenes, thiochromeno[4,3-b]pyrans, pyrano[3,2-c]-quinolines, and thiazolo[3,2-a]pyridines. 相似文献
6.
A convenient synthesis of furo[3,2-b]pyridine and its 2- and 3-methyl derivatives from ethyl 3-hydroxypiconate ( 1 ) is described. The hydroxy ester 1 was O-alkylated with ethyl bromoacetate or ethyl 2-bromopropionate to give the diester 2a or 2b . Cyclization of compound 2a afforded ethyl 3-hydroxyfuro[3,2-b]pyridine-2-carboxylate ( 3 ) which in turn was hydrolyzed and decarboxylated to give furo[3,2-b]pyridin-3-(2H)-one ( 4a ). Cyclization of 2b gave the 2-methyl derivative 4b . Reduction of 4a and 4b with sodium borohydride yielded the corresponding hydroxy derivative 5a and 5b respectively, which were dehydrated with phosphoric acid to give furo[3,2-b]pyridine ( 6a ) and its 2-methyl derivative ( 6b ). 2-Acetylpyridin-3-ol ( 8 ) was converted to the ethoxycarbonylmethyl ether ( 9 ) by O-alkylation with ethyl bromoacetate, which was cyclized to give 3-methylfuro[3,2-b]pyridine-2-carboxylic acid ( 10 ). Decarboxylation of 10 afforded 3-methylfuro[3,2-b]pyridine ( 11 ). 相似文献
7.
Akira Tanaka Kenichi Yakushijin Shigetaka Yoshina 《Journal of heterocyclic chemistry》1977,14(6):975-979
4H-Furo[3,2-b]indole (III) was prepared from deoxygenation of 2-(2-nitrophenyl)furan (II) with triethyl phosphite and thermolysis of 2-(2-azidophenyl)furan (VI). 4H- or 4-alkylfuro [3,2-b]indole-2-carboxaldehydes (VIII, IXa-c) were obtained by Vilsmeier formylation of the corresponding furo[3,2-b]indoles (III, VIIa-c). 4H-Furo[3,2-b]indole-2-carboxaldehyde (VIII) was submitted to the Cannizzaro, Wittig and reduction reactions. The Shiff's bases were obtained by the reaction of 4-ethylfuro[3,2-b]indole-2-carboxaldehyde (IXb) with amines. J. Heterocyclic Chem., 14, 975 (1977) 相似文献
8.
The reaction of 3,4-diamino-5-oxo-4,5-dihydro-l,2,4-triazine or its 6-methyl or 6-phenyl substituted derivatives and ethyl acetoacetate gave three compounds: 4,7-dioxo-9-methyl-1,4,6,7-tetrahydro-as-triazino[4,3-b]-1,2,4-triazepine in poor yield, isomeric 4,9-dioxo-7-methyl-1,4,8,9-tetrahydro-as -triazino[4,3-b]-1,2,4-triazepine and by competitive cyclisation, 2-methyl-7-oxo-3,7-dihydro-s-triazolo[3,2-c]-1,2,4-triazine. By condensation of 3-methylamino-4-amino-5-oxo-4,5-dihydro-1,2,4-triazine with ethyl acetoacetate, the formation of 4,9-dioxo-7,10-dimethyl-4,8,9,10-tetrahydro-as-triazino[4,3-b]-1,2,4-triazepine was strongly favored. 相似文献
9.
Aliev Z. G. Maslivets A. N. Golovnina O. V. Krasnykh O. P. Atovmyan L. O. 《Russian Chemical Bulletin》2001,50(7):1317-1319
Thermal decarbonylation of ethyl 1,2,4-trioxo-1,2,4,5-tetrahydropyrrolo[1,2-a]quinoxaline-3-carboxylate afforded ethyl 2-oxo-2,5-dihydrofuro[2,3-b]quinoxaline-3-carboxylate. The structure of the resulting compound was established by X-ray diffraction analysis. 相似文献
10.
Heating 5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one with isonicotinoyl chloride in pyridine gives 6-isonicotinoyl-5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one. The 1-alkyl-4[(11-oxo-5,13-dihydro-11H-isoquino[3,2-b]quinazolin-6-yl)carbonyl]pyridinium iodides obtained by alkylation of 6-isonicotinoyl-5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one using alkyl iodides in the presence of NaH are converted to 1′-R-spiro[7H,8H-2a,7a-diazacyclopenta[fg]naphthacene-2,4′(1′H)-pyridine]-1,8(2H)-diones. The chemical and spectroscopic properties of the spiro compounds obtained
were studied.
For Communication 32 see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 52–58, January, 2009. 相似文献
11.
E. Campaigne K. Folting J. C. Huffman T. P. Selby 《Journal of heterocyclic chemistry》1981,18(3):575-580
Ethyl 4-chloroacetoacetate condenses with 4-amino-6-hydroxy-2-pyrimidinethiol to yield ethyl 3-hydroxy-5-oxo-7-aminothiazolino[3,2-a]pyrimidin-3-acetate ( 3 ), and not ethyl 3-hydroxy-5-amino-7-oxothiazolino[3,2-a]-pyrimidin-3-acetate, as previously reported. This compound reacts with ammonia to produce ethyl 4-(6′-amino-4′-oxo-2′-pyrimidinethiol)-3-aminocrotonate ( 8 ), the open chain structure of which accounts for the cyclization of 3 to the poly-cyclic lactam, 6a-hydroxy-5,6,6a,7-tetrahydro-8-thia-1,4-diazacycl[3.3.2]azine-2,5-dione, rather than the sterically more favorable lactone, when 3 was treated with triethylamine. Some other reactions of 3 are described, and the structures of 3 and 8 were comfirmed by single crystal X-ray diffraction analysis. 相似文献
12.
The preparation of ethyl 2-bromothieno[2,3-b]pyrrole-5-carboxylate, ethyl 2-bromothieno[3,2-b]pyrrole-5-carboxylate, ethyl 2-nitrothieno[2,3-b]pyrrole-5-carboxylate and ethyl 2-nitrothieno[3,2-b]pyrrole-5-carboxylate are described. 相似文献
13.
Two novel tricyclic ring systems were designed as serine protease inhibitors and synthesized from oxindoles; the first series, 1,3-oxazino[6,5-b]indole-2,4-(3H,9H)-diones, were prepared from 2,3-dihydro-2-oxo-(1H)-indole-3-carboxamides and phosgene in tetrahydrofuran with triethylamine. The second, a 2H-1,3,5-oxadiazino[3,2-a]indole-2,4-(3H)-dione was made using a similar cyclization on 2,3-dihydro-2-oxo-N-phenyl-(1H)-indole-1-carboxamide. 相似文献
14.
S. Yu. Ryabova L. M. Alekseeva V. G. Granik 《Chemistry of Heterocyclic Compounds》2001,37(8):997-1004
The reactions of 2-dimethyliminomethyl-3-(p-nitrophenyl)aminoindole chloride with compounds with an active methylene center have been studied. A series of derivatives of -carboline have been synthesized. By the reaction of 3-ethoxycarbonyl-2-methyl-1-p-nitrophenylpyrido[3,2-b]indolinium chloride with the diethyl acetal of DMF the corresponding 2-dimethylaminovinyl derivative was synthesized which was converted into 5-p-nitrophenyl-1-oxo-1,10-dihydropyrano[3',4':5,6]pyrido[3,2-b]indol-5-ium chloride in the presence of acid. 相似文献
15.
The N-oxide 2 of furo[3,2-b]pyridine ( 1 ) was cyanated by the Reissert-Henze reaction with potassium cyanide and benzoyl chloride to give 5-cyano derivative 3 , which was converted to the carboxamide 4 , carboxylic acid 5 , ethyl ester 6 and ethyl imidate 8 . Chlorination of 2 with phosphorus oxychloride yielded 2-9a , 3- 9b , 5- 9c and 7-chloro derivative 9d . Reaction of 9d with sodium methoxide, pyrrolidine, N,N-dimethylformamide and ethyl cyanoacetate afforded 7-methoxy- 10 , 7-(1-pyrrolidyl)- 11 and 7-dimethylaminofuro[3,2-b]pyridine ( 14 ) and 7-(1-cyano-1-ethoxy-carbonyl)methylene-4,7-dihydrofuro[3,2-b]pyridine ( 12 ). Nitration of 2 with a mixture of fuming nitric acid and sulfuric acid gave 2-nitrofuro[3,2-b]pyridine N-oxide ( 15 ). 相似文献
16.
A number of novel 1,3-oxazino[5,6-b]indoles and 2-oxo- or 4-oxopyrano[3,2-b]indoles containing #3-position substituents were prepared. Starting materials were 3-hydroxy-indole-2-carboxylic acid esters in which the #2-position ester function is converted to carboxamide, β-ketoester, or β-ketosulfone. 相似文献
17.
Lantsetti N. A. Ryabova S. Yu. Alekseeva L. M. Shashkov A. S. Granik V. G. 《Russian Chemical Bulletin》2002,51(3):506-512
1-Aryl-2-oxo-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole N-oxides were synthesized based on 3-(N"-aryl-N"-chloroacetyl)amino-2-formylindoles. Deoxidation of 2-oxo-1-phenyl-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole N-oxide afforded 1,2,3,6-tetrahydro- and 1,2,3,4,5,6-hexahydro[1,4]diazepino[6,5-b]indole derivatives. A new approach to the synthesis of pyrido[3,2-b]indole and pyrimido[5,4-b]indole derivatives was developed. 相似文献
18.
O. B. Smirnova T. V. Golovko L. M. Alekseeva V. V. Chernyshev V. G. Granik 《Russian Chemical Bulletin》2010,59(1):177-185
The reactions of 2-dicyanomethylidene-3-ethoxymethylidene-2,3-dihydroindole with hydrazine hydrate and phenylhydrazine afforded
2,3-diamino-4-cyanopyrido[4,3-b]indole and 3-amino-2-anilino-4-cyanopyrido[4,3-b]indole, respectively, and the reactions of the latter compounds with dimethylformamide diethyl acetal were studied. The reactions
of 2,3-diamino-4-cyanopyrido[4,3-b]indole with benzaldehyde, ethyl acetoacetate, and acetylacetone were investigated. First representatives of new heterocyclic
systems, viz., [1,2,4]triazolo[1’,5’:1,6]-pyrido[4,3-b]indole and pyrazolo[1’,5’:1,2]pyrido[4,3-b]indole, were synthesized. The structure of ethyl 6-cyano-5-[(E)-(dimethylamino)methylideneamino]-2-methyl-7H-pyrazolo-[1’,5’:1,2]pyrido[4,3-b]indole-1-carboxylate was established by X-ray diffraction. 相似文献
19.
We report herein the synthesis of a novel class of compounds, ethyl 4-oxo-4H-furo[3,2-c]pyran-6-yl carbonate, (7E)-7-[(dimethylamino)methylene]-4H-furo[3,2-c]pyran-4,6(7H)-dione, 5-oxo-N-phenyl-2,5-dihydro-4H-furo[3,2-b]pyrrole-4-carboxamide, and 5-oxo-N-phenyl-5,6-dihydro-4H-thieno[3,2-b]pyrrole-4-carboxamide starting from the corresponding acid derivatives. Intramolecular cyclization in the presence of thionyl chloride formed the target fused ring systems. Additional transformation was seen in the cyclization of furan-fused heterocycle. A mechanism was proposed based on experimental and computational findings. 相似文献
20.
Robert J. Alaimo 《Journal of heterocyclic chemistry》1973,10(5):769-772
A series of 8-substituted and 7,8-disubstituted-4-oxo-3-(4H-pyrimido[2,1-b]benzothiazole)carboxylic acids and esters including a 9-aza analog were synthesized from substituted 2-aminobenzothiazoles and diethyl ethoxymethylenemalonate. The 9-aza analog, ethyl 8-methoxy-4-oxo-3-(4H-pyrido[3′,2′:4,5]thiazolo[3,2-a]pyrimidine)carboxylate ( 56 ), represents the first preparation of this new heterocyclic ring. These compounds were examined for antiparasitic activity, however, no significant activity was detected. 相似文献