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1.
Aromatic aldehydes react with indole-2-carboxylic acid azides under acid catalysis conditions to give the corresponding 3-(-halobenzyl)indoles, which react with aliphatic and aromatic amines to give the corresponding aminobenzylindoles. The latter undergo intramolecular cyclization to dihydropyrrolo[3,4-b]indoles at room temperature and are converted to dihydropyrimido[4,5-b]indoles through the Curtius rearrangement when they are heated to 80-110°C. Acetylation of the latter products gives N- and O-acetyl derivatives.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 935–939, July, 1982. 相似文献
2.
Acetylation of pyridazino[4,5-b]indol-4-ones with acetic anhydride gives the O-acetyl derivatives, and acetylation of 1,2-dihydropyridazino[4,5-b]indol-4-ones leads to the 2-acetyl and 2,4-diacetyl derivatives. Tetrahydropyridazino[4,5-b]indoles, obtained by reduction of the dihydro derivatives, undergo substitution by an acetyl group at the 2 position.See [1] for communication II.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1218–1222, September, 1976. 相似文献
3.
The dihydropyridazine ring undergoes contraction to a dihydropyrrole ring to give 1-phenyl-2-benzylideneaminodihydropyrrolo[3,4-b]indol-3-ones when 1-phenyldihydropyridazino[4,5-b]indol-4-ones are treated with aromatic aldehydes under acid catalysis conditions. The reaction mechanism consists in the formation of a (3-indolyl)phenylmethyl cation, which leads to opening of the pyridazine ring and subsequent development of a bond between the carbonium center and the amide nitrogen atom.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1406–1408, October, 1976. 相似文献
4.
G. I. Zhungietu L. M. Zorin V. I. Gorgos M. A. Rekhter 《Chemistry of Heterocyclic Compounds》1982,18(8):811-813
5H-Pyridazo[4,5-b]indol-1-ones were obtained by heating 2-acetylindole-3- or 2-aroylindole-3-carboxylic acids with hydrazine hydrate in ethylene glycol or alcohol. 1-Chloro-5H-pyridazo[4,5-b]indoles are formed by treatment of 5H-pyridazo[4,5-b]indol-1-ones with phosphorus oxychloride.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1064–1066, August, 1982. 相似文献
5.
2-Arylidene-1-acetylindolin-3-ones were obtained from 1-acetylindolin-3-ones and p-substituted benzaldehydes or 4-pyridinecarboxaldehyde, by the action of malonodinitrile, andwere converted into 2-amino-4-aryl-5-acetyl-3-cyanopyrano[3,2-b]indoles. When heated with an aqueous-alcoholic solution of KOH, the latter compounds transform into 2-alkoxy-4-aryl-3-cyano--carbolines. The possible paths of formation of -carbolines and pyrano[3,2-b]indoles are discussed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 230–235, February, 1985. 相似文献
6.
R. I. Vasˈkevich A. I. Vasˈkevich A. V. Turov V. I. Staninets M. V. Vovk 《Chemistry of Heterocyclic Compounds》2011,47(8):1037-1042
The interaction of 3-allylsulfanyl-5H-[1,2,4]triazino[5,6-b]indole with iodine led to 1-iodomethyl-1,2-dihydro[1,3]thiazolo[2',3':3,4][1,2,4]triazino[5,6-b]indol-11-ium pentaiodide with an angular structure, on the basis of which 1-iodomethyl-1,2-dihydro[1,3]thiazolo-, 1-methylidene-1,2-di-hydro[1,3]thiazolo,
and 1-methyl[1,3]thiazolo derivatives were obtained. The intramolecular cyclization of 3-propargyl(allyl)sulfanyl-5H-[1,2,4]triazino[5,6-b]indoles under the influence of concentrated sulfuric acid led to linear annelated products:3-methyl[1,3]thiazolo[3',2':2,3][1,2,4]tri-azino[5,6-b]indole or its 2,3-dihydro derivative. 相似文献
7.
Kawasaki T Ogawa A Terashima R Saheki T Ban N Sekiguchi H Sakaguchi KE Sakamoto M 《The Journal of organic chemistry》2005,70(8):2957-2966
Hexahydropyrrolo[2,3-b]indoles 6 were synthesized in five steps from indolin-3-one 8 by a general and efficient method, in which elements of molecular diversity were readily added onto the 3a-position of the pyrrolo[2,3-b]indole ring system. Horner-Wadsworth-Emmons reaction of 2-allyloxyindolin-3-ones 7, derived from indolin-3-one 8 and a variety of allylic alcohols, smoothly proceeded with successive Claisen rearrangement to give the corresponding 3-allyl-3-cyanomethylindolin-2-ones 15. Indolin-2-ones 15 were converted into pyrrolo[2,3-b]indoles 6 using partial hydrolysis followed by reductive cyclization with LiAlH(4). Synthesis of N-methylated pyrrolo[2,3-b]indole derivatives 23 and 26 is also described. 相似文献
8.
Indole-2,3-dione ( 1 ) was treated with malonic acid ( 2 ) in a mixture of ethanol/pyridine to afford 1-[3-(2-oxoindolinylidene)]acetic acid ( 3 ). Compound 3 reacted with thionyl chloride to give the corresponding acid chloride ( 4 ). The acid chloride 4 reacted with arenes in the presence of AlCl3 to yield 3-(2-oxoindolinylidene)acetophenones 5a–c . Compounds 5a–c reacted with 3-methylpyrazolin-5-one derivatives 6a , b to give 3-aracyl-3-[4′-(3′-methylpyrazolin-5-onyl)]-indoline-2-one derivatives 7a–f . Compounds 7a–f were treated with phosphorus pentoxide in phosphoric acid, with ammonium acetate or methanolic methylamine and with phosphorus pentasulfide to give spiro[indoline-3,4′-(pyrazolo[4,5-b]pyran)]-2-ones 8a–f , spiro[indoline-3,4′-(pyrazolo[4,5-b]-dihydropyridine)]-2-ones 9a–f , 10a–f and spiro[indoline-3,4′-(pyrazolo[4,5-b]thiopyran)]-2-ones 10a–f , respectively. All of the synthesized spiroheterocycle derivatives were identified by conventional spectroscopic methods (IR, 1H NMR) and elemental analyses. © John Wiley & Sons, Inc. 相似文献
9.
V. B. Sokolov A. Yu. Aksinenko T. A. Epishina T. V. Goreva 《Russian Journal of General Chemistry》2016,86(5):1028-1031
Alkylation of substituted indoles (carbazoles, tetrahydrocarbazoles, and gamma-carbolines) with (phenothiazinyl)propenones catalyzed by cesium fluoride has led to the formation of 1-(phenothiazin-10-yl)-3-(carbazol-9-yl)propane-1-ones, (1-phenothiazin-10-yl)-3-(tetrahydrocarbazol-9-yl)propane-1-ones, and 3-(tetrahydropyrido[4,3-b]indol-5-yl)-1-(phenothiazin-10-yl)propane-1-ones, respectively. 相似文献
10.
Neringa Kleizien? Virgin? Amankavi?ien? Ulf Berg Carsten Schicktanz Klaus Schlothauer Algirdas ?a?kus 《Monatshefte für Chemie / Chemical Monthly》2006,43(9):1109-1117
Condensation of 1-substituted 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-ones with 5-nitrosalicylaldehyde afforded 1′-[(N-monosubstituted carbamoyl)methyl]indoline nitrospirobenzopyrans.
Treatment of the latter with strong base led to the formation of a mixture of cis/trans-5a,13-methano-1,3-benzoxazepino[3,2-a]indoles. Results of semiempirical calculations gave evidence that such a transformation of nitrospirobenzopyrans to bicyclic
indole derivatives could proceed via a single transition state, where the negatively charged carbon atom attacks the vinylic double bond of the spiropyran system. 相似文献
11.
Neringa Kleizienė Virginė Amankavičienė Ulf Berg Carsten Schicktanz Klaus Schlothauer Algirdas Šačkus 《Monatshefte für Chemie / Chemical Monthly》2006,137(8):1109-1117
Summary. Condensation of 1-substituted 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-ones with 5-nitrosalicylaldehyde afforded 1′-[(N-monosubstituted carbamoyl)methyl]indoline nitrospirobenzopyrans.
Treatment of the latter with strong base led to the formation of a mixture of cis/trans-5a,13-methano-1,3-benzoxazepino[3,2-a]indoles. Results of semiempirical calculations gave evidence that such a transformation of nitrospirobenzopyrans to bicyclic
indole derivatives could proceed via a single transition state, where the negatively charged carbon atom attacks the vinylic double bond of the spiropyran system. 相似文献
12.
Farag A. El-Essawy 《合成通讯》2013,43(6):877-887
8,10-Dimethyl-3-(unsubstituted, methyl, ethyl, n-butyl, phenyl)-4-hydroxypyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidin-2(1H)-ones and 3-(2-hydroxyethyl)-2,8,10-trimethylpyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidin-4-ol were synthesized by cyclocondensation of 3-amine-4,6-dimethyl-1H-pyrazolo[3,4-b]pyridine with ethyl malonates and α-acetyl-γ-butyrlolactone. Dichloro- and diazido- derivatives were obtained from the reaction of pyridopyrazlopyrimidine derivatives with POCl3 followed by NaN3. The tetrahetrocyclic systems were formed by cyclization of 4-chloro-3-(2-chloroethyl)-2,8,10-trimethylpyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine with the appropriate primary amines. The structures of all compounds were established by NMR and mass spectra. 相似文献
13.
Reactions of benzotriazol-1-yl(1H-pyrrol-2-yl)methanone 10 and benzotriazol-1-yl(1H-indol-2-yl)methanone 11 with diverse ketones, isocyanates, and isothiocyanates in the presence of base afforded pyrrolo[1,2-c]oxazol-1-ones 1, oxazolo[3,4-a]indol-1-ones 2, pyrrolo[1,2-c]imidazoles 3, and imidazo[1,5-a]indoles 4 by a simple one-step procedure. 相似文献
14.
Velanganni Paul Alex Raja 《Tetrahedron》2006,62(20):4892-4899
The five-component reaction of ethyl 2-[(2-oxopropyl)sulfanyl]acetate, aromatic aldehydes, and ammonium acetate affords two diastereomers of 5,7-diaryl-5,6,7,8-tetrahydro-1H-pyrido[3,4-b][1,4]thiazin-2(3H)-ones via a novel tandem Mannich-enamine-substitution sequence. Presumably, they are generated from ethyl 2-[(4-oxo-2,6-diaryl-3-piperidinyl)sulfanyl]acetates. During the formation of the trans-5,7-diaryl-5,6,7,8-tetrahydro-1H-pyrido[3,4-b][1,4]-thiazin-2(3H)-ones from ethyl 2-[(4-oxo-2,6-diaryl-3-piperidinyl)sulfanyl]acetates, the configuration at the carbon bearing an aryl group adjacent to the enamide CC double bond is inverted via ring opening and closure. When o-substituted benzaldehydes were employed in this reaction, 5,7-diaryl-5,6-dihydro-1H-pyrido[3,4-b][1,4]thiazin-2(3H)-ones were obtained via air oxidation, along with trans-5,7-diaryl-5,6,7,8-tetrahydro-1H-pyrido[3,4-b][1,4]-thiazin-2(3H)-ones. 相似文献
15.
George Bobowski 《Journal of heterocyclic chemistry》1987,24(2):473-479
Treatment of 2-(4,9-dihydro-3H-pyrido[3,4-b]indol-1-yl)-1-methylcyclohexanol ( 2a ) with acetic anhydride or methyl isocyanate gave 2-acetyl-2,3,4,9-tetrahydro-1-(6-oxoheptylidene)-1H-pyrido[3,4-b]indole ( 3 ) or 1,3,4,9-tetrahydro-N-methyl-1-(6-oxoheptylidene)-2H-pyrido[3,4-b]indole-2-carboxamide ( 4 ), respectively. Simpler analogues, 1-alkyl-4,9-dihydro-3H-pyrido[3,4-b]indoles, 7 , subjected to identical reaction conditions, gave 2-acetyl-1-alkylidene-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indoles 8 and 1,3,4,9-tetrahydro-N-methyl-1-alkyli-dene-2H-pyrido[3,4-b]indole-2-carboxamides 9 , respectively. A limited lanthanide shift reagent study to determine stereochemical assignments was also performed. 相似文献
16.
Yu-wei RenXuerui Wang Weixia WangBing Li Zong-jun ShiWei Zhang 《Tetrahedron letters》2011,52(2):192-195
Photochemical and thermal cyclization of 4-(2-azidophenyl)-3,4-dihydropyrimidin-2-ones could afford fused indoles, such as 1,2,3a,9b-tetrahydro-4-methylenepyrimidino[5,4-b]indol-2-ones and 1,3,5,6,7a,12b-hexahydroquinazolino[9,4-b]indol-2,7-dione in high yields via nitrene electrophilic addition and rearrangement reactions. 相似文献
17.
A. V. Bentya R. I. Vas’kevich A. V. Bol’but M. V. Vovk V. I. Staninets A. V. Turov E. B. Rusanov 《Russian Journal of Organic Chemistry》2008,44(9):1362-1368
6-Allylsulfanyl-1-arylpyrazolo[3,4-d]pyrimidin-4(5H)-ones react with iodine and sulfuric acid to give angular pyrazolothiazolopyrimidine derivatives. The reaction of 6-(prop-2-yn-1-ylsulfanyl)-1-(4-tolyl)-pyrazolo[3,4-d]pyrimidin-4(5H)-one with sulfuric acid gives angularly fused pyrazolo[4,3-e][1,3]thiazolo-[3,2-a]pyrimidin-4-one, whereas in the reaction with sodium methoxide linearly fused pyrazolo[3,4-d][1,3]-thiazolo[3,2-a]pyrimidin-4-one was formed. Linearly fused pyrazolo[3′,4′:4,5]pyrimido[2,1-b][1,3]thiazole derivatives were also obtained by reaction of 1-aryl-6-(3-phenylprop-2-en-1-ylsulfanyl)pyrazolo[3,4-d]pyrimidin-4(5H)-ones with sulfuric acid. 相似文献
18.
Maria Rosaria Del Giudice Franco Gatta Guido Settimj 《Journal of heterocyclic chemistry》1990,27(4):967-973
Oxidation of 1-methyl-3-methoxycarbonyl-β-carboline with selenium dioxide gave 1-formyl-3-methoxycarbonyl-β-carboline II . Compound II reacted with acetic or propionic anhydride to give easily the 2-methoxycarbonyl-6H-indolo[3,2,1-d,e][1,5]naphthyridin-6-ones III ; reaction of II with some primary amines led to the formation of the Schiff bases IV , which were reduced to the 1-aminomethyl-3-methoxycarbonyl-β-carbolines V with sodium borohydride. Cyclization of V with aqueous formaldehyde led to the pyrimido[3,4,5-lm]pyrido[3,4-b]indoles VI . Analogously, cyclization with formaldehyde, acetone or 1,1′-carbonyldiimidazole of the 3-aminomethyl- 1,2,3,4-tetrahydro-β-carbolines VIII , obtained by reaction of 3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline VII with amines followed by lithium aluminium hydride reduction of the resulting amides, gave the imidazo[1′,5′-1,6]pyrido[3,4-b]indoles IX and X . Dieckmann cyclization of 3-methoxycarbonyl-2-[(3-ethoxycarbonyl)-1-propyl]-1,2,3,4-tetrahydro-β-carboline XI led to a 1:1 mixture of the β-ketoesters XII and XIII , which underwent deethoxycarbonylation to 5,6,8,9,10,11,11a,12-octahydroindolo[3,2-b]quinolizin-11-one XIV . Finally, the polyphosphoric acid (or esters) catalyzed cyclization of the N-acyl derivatives XVI of 3-hydrazinocarbonyl-β-carboline XV led smoothly to the 3-(1,3,4-oxadiazol-2-yl)-β-carbolines XVII . 相似文献
19.
At boiling in trifluoroacetic acid derivatives of 3-cyanovinyl-3-p-nitrophenylaminoindole are cyclized into the corresponding pyrido[3,2-b]indoles as a results of activation of the CN group. Thermal cyclization of ethyl indolylacrylate occurs with participation of the more reactive ethoxycarbonyl group to give 3-cyanopyrido[3,2-b]indole.RF State Scientific Center NIOPIK, Moscow 103787, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 362–367, March, 2000. 相似文献
20.
S. V. Simakov V. S. Velezheva V. V. Dvorkin N. N. Suvarov 《Chemistry of Heterocyclic Compounds》1985,21(5):533-537
The condensation of N-(2-ethoxycarbonylindol-3-yl)-N,N-dialkylamidines with ammonia, primary amines, and hydrazines has given a series of 4-oxopyrimido[5,4-b] indoles which have been converted into the 4-chloro and then into the 4-methoxy, 4-dialkylamino, and 4-mercapto derivatives. 2,4-Dioxopyrimido[5,4-b]indoles have been synthesized by the successive action of chloroformic ester and then methylamine, hydrazine, or ethylhydrazine on 3-amino-2-ethoxycarbonylindoles differing by their substituents in position 5.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 635–639, May, 1985. 相似文献