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1.
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
2.
A. Monge J. A. Palop T. Goi E. Fernndez-Alvarez 《Journal of heterocyclic chemistry》1986,23(1):141-144
2-(3-Carboxy-1-methylindole)acetic acid anhydride ( 1 ) reacts with aryldiazonium salts to give 85–95% of the corresponding α-hydrazono anhydrides 2 . Treating 2 with boiling hydrazine hydrate in xylene, the respective 2-aryl-4-carbohydrazido-5-methyl-1-oxo-1,2-dihydro-5H/-pyridazino[4,5-b]indoles 3 were obtained (47–67%), and these compounds characterized as the respective benzylidene derivatives 4 . Compounds 2 react with amines (aniline, morpholine, piperidine) to give the respective 2-(3-carboxy-1-methylindole)aceta-mide 5 or the respective 2-aryl-4-carboxamido-5-methyl-5H-pyridazino[4,5-b]indole 6 , the product obtained depending on the structure of the aryl substituent. Boiling 2b (aryl = 4-chlorophenyl) with 5% sodium hydroxide gave (80%) 2-(3-carboxy-1-methylindole)acetic acid ( 7 ). Hydrolysis of 2b gave a mixture of 7 and 2-(3-carboxy-1-methylindolyl)-2-(4-chlorophenylhydrazono)acetic acid ( 8 ). 相似文献
3.
Alkyl 3-(2-aminoethyl)-1H-indole-2-acetates 6a and 6b are synthesized starting from methyl 1H-indole-2-acetate (2) via methyl 3-(2-nitroethenyl)-1H-indole-2-acetate (4) and the alkyl 3-(2-nitroethyl)-1H-indole-2-acetates 5a and (Scheme 1). Analogously, diisopropyl 3-(2-aminoethyl)-1H-indole-2-malonate 20b is obtained from diisopropyl 1H-indole-2-malonate 11c (Scheme 4). An alternative synthesis of 20a and 20b follows a route via 15–18 and the dialkyl 3-(2-azidoethyl)-1H-indole-2-malonates 19a and 19b , respectively (Scheme 3). The aminoethyl compounds 6a and 20a are easily transformed into lactams 7 and 21 , respectively. Procedures for the preparation of the indoles 2 and 11a and of the alkylating agent 14 are described. A tautomer 12 of 11a is isolated. 相似文献
4.
A. Monge Vega M. T. Martinez J. A. Palop J. M. Mateo E. Fernndez-Alvarez 《Journal of heterocyclic chemistry》1981,18(5):889-892
A synthesis of four 1H-[1,2]diazepino[4,5-b]indole derivatives and some preliminary information about their biological activity are presented. The starting materials were 2-ethoxycarbonylindoles and 2-ethoxy-carbonyl-3-formylindoles, la, b and 2a, b, respectively. 2-Ethoxycarbonyls la, b reacted with 1-dimethylamino-2-nitroethylene and -2-ethoxycarbonyl-3-formylindoles 2a, b in the presence of nitroalkanes (nitromethane or nitroethane) giving 3-(2-nitrovinyl)indoles 3a, b. Reduction of 3a, b yielded β-(2-oxoalkyl)indoles 4. On reaction with an excess of hydrazine hydrate, compounds 4 gave satisfactory yields of 5-oxo-1H-[1,2]diazepino[4,5-b]indoles 5. 相似文献
5.
A. Monge Vega I. Aldana M. M. Rabbani E. Fernandez-Alvarez 《Journal of heterocyclic chemistry》1980,17(1):77-80
This paper describes the synthesis of the previously unknown 11H-1,2,4-triazolo[4,3-b]pyridazino[4,5-b]indoles (2) and 11H-tetrazolo[4,5-b]pyridazino[4,5-b]indoles (3) from 4-hydrazino-5H-pyridazino[4,5-b]indoles (1) , as well as the synthesis of 1,2,4-triazolo[3,4-f]-1,2,4-triazino-[4,5-a]indoles (10) from 2-indolecarbohydrazide (4) . Compounds 2 were obtained by acylation of compounds 1 , followed of thermal cyclization and compounds 3 by treating compounds 1 with nitrous acid. The reactions of compound 4 with formic acid or ethyl orthoformiate gave 1,2-dihydro-1-oxo-1,2,4-triazino[4,5-a]indole (6) . Treating this last compound with phosphorus oxychloride or phosphorus pentasulfide, followed by hydrazine, gave 1-hydrazino-1,2,4-triazino-[4,5-a]indole (9) . Acylation of this last compound, followed of cyclization gave compounds 10 . All the compounds were characterized by elemental analysis and ir and 1H-nmr spectra. 相似文献
6.
Wayland E. Noland Christopher D. Brown Rodney D. DeKruif Nicholas P. Lanzatella Siming M. Gao Abigail E. Zabronsky 《合成通讯》2018,48(14):1755-1765
Condensation of indole 1a with eight acetophenones 8a–h in ethanolic HCl afforded the corresponding mixtures of condensation products: 3,3-(1-phenylethane-1,1-diyl)bis(1H-indoles) 11a–h (2:1 condensation of indole:acetophenone, –H2O) and diastereomers of substituted 1,2,3,4-tetrahydro-3-(1H-indol-3-yl)-1-methyl-1,3-diphenylcyclopent[b]indoles 12a–h and 13a–h (2:2 condensation of indole:acetophenone, –2H2O). Each mixture was analyzed by 1H NMR. The use of substituted electron-withdrawing acetophenones favored formation of 2:1 condensation products, whereas the use of substituted electron-donating acetophenones favored formation of 2:2 condensation products. Increased reaction temperature gave higher 2:2 condensation yields, but temperatures above 40?°C were unfavorable, giving complex, tarry mixtures. 相似文献
7.
A. Monge J. A. Palop T. Goí A. Martínez E. Fernndez-Alvarez 《Journal of heterocyclic chemistry》1985,22(5):1445-1451
The Vilsmeier-Haack reaction with ethyl 2-(1-methylindole)acetate and N,N-Dimethylamides/phosphorus oxychloride gave (65–85%) of ethyl 2-(3-acyl-1-methylindole)acetates 2 , which when boiled with hydrazine yielded about 90% of 4,5-dihydro-6-methyl-4-oxo-3H[1,2]diazepino[5,6-b]indoles 3. The attempted cyclization of 2-(1-methylindole)acetohydrazones 6 with acyl (acetyl and benzoyl) chlorides/triethylamine, to [1,2]diazepino[5,6-b]indole derivatives was fruitless and the bis(acyl)hydrazones 9 were obtained. Several transformations of 9 are reported. Similarly, the attempted cyclization of 3-indoleacetohydrazones 14 with acetyl chloride/triethylamine to [1,2]diazepino[4,5-b]indole derivatives was also fruitless and the bis(acyl)hydrazones 16 were again obtained. 相似文献
8.
Indole, 2-methylindole, and 3-etliylindole have been condensed with acetyl- and propionylpyridine, respectively. When propionylpyridine was used as the reactant, the product always was a 1-(pyridyl)-1-indoly[propylene. Condensation of 2-substituted indoles with 3-acetylpyridine gave similar products, whereas a similar condensation with 4-acetylpyridine gave 1,2-bis(3-indolyl)-1-(4-pyridyl)ethanes (e.g. 7a ). Condensation of unsubstituted indole with 3-or 4-acetylpyridine respectively, gave 1,1-bis(3-indolyl)-1-(pyridyl)ethanes (e.g. 6c ). 相似文献
9.
Kaname Takagi Tomoji Aotsuka And Hikari Morita Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1986,23(5):1443-1449
Reactions of 4-ethoxycarbonylamino-1H-1,5-benzodiazepine-3-carbonitrile (2) with aliphatic primary amines gave 1-substituted 4-(2-aminoanilino)pyrimidin-2(1H)-one-5-carbonitriles 3. Analogous reactions of 2 with aromatic primary amines afforded 2-(2′-anilino-1′-cyanovinyl)benzimidazoles 5 and 6. Upon treatment with triethylamine, 3 underwent intramolecular cyclization to give 3-substituted 5-aminopyrimidino[4,5-b]-[1,5]benzodiazepin-2(3H,11H)-ones 8 . Heating of 3 with p-toluenesulfonic acid in ethanol gave 2-substituted pyrimidino[1,6-a]benzimidazol-1(2H)one-4-carbonitriles 9 . Reactions of 2 with hydrazines were also described. Mechanistic pathways are proposed to account for the products. 相似文献
10.
George Bobowski 《Journal of heterocyclic chemistry》1983,20(1):183-187
The treatment of N-[2-(1H-indol-3-yl)ethyl]alkanamide, 1 (1), with phosphorus oxychloride under controlled conditions gave l-alkyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-ol, 2 . The reaction of 2 with acetic anhydride or with methyl isocyanate at room temperature resulted in the formation of amido carbinol 3 and urea carbinol 7, respectively. The former was transformed into amido ester 4 by boiling acetic anhydride. When the reaction of 3 with acetic anhydride was carried out in the presence of excess triethylamine at 105°, C-N bond cleavage of the tetrahydropyridine ring took place with concurrent bis(N-acetylation) to give the enol ester derivative 5 . The structures of all compounds are consistent with chemical and spectral evidence. 相似文献
11.
Kiran S. Hon Hemantkumar N. Akolkar Bhausaheb K. Karale 《Journal of heterocyclic chemistry》2020,57(4):1692-1697
Novel 1-benzyl-3-(4-fluorophenyl)-1H-pyrazole-4-carbaldehydes 3a to 3e were synthesized via Vilsmeier-Haack reaction of the appropriate 1-benzyl-2-(1-(4-fluorophenyl)ethylidene)hydrazines, derived from 4-fluoroacetophenone 1 with substituted 2-benzylhydrazines 2a to 2e . The base catalyzed condensation of 1-benzyl-3-(4-fluorophenyl)-1H-pyrazole-4-carbaldehydes 3a to 3e with 1-(4-fluoro-2-hydroxyphenyl)ethanone 4 gave (E)-3-(1-benzyl-3-(4-fluorophenyl)-1H-pyrazol-4-yl)-1-(4-fluoro-2-hydroxyphenyl)prop-2-en-1-ones 5a to 5e . On cyclization with dimethyl sulfoxide (DMSO)/I2, compounds 5a to 5e gave 2-(1-benzyl-3-(4-fluorophenyl)-1H-pyrazol-4-yl)-7-fluoro-4H-chromen-4-ones 6a to 6e . Structures of all novel compounds were confirmed by infrared (IR), proton nuclear magnetic resonance (1H NMR), carbon nuclear magnetic resonance (13C NMR), and mass spectral data. All the synthesized compounds were screened for their antibacterial activities. 相似文献
12.
Reactions of 3-methyl-6-[4-(4-hydroxyphenyl)-1-piperazinyl]-2(3H)-benzoxazolone, 3-methyl-6-[4-(4-hydroxy-phenyl)-1-piperazinyl]-2(3H)-benzothiazolone and 1,3-dimethyl-5-[4-(4-hydroxyphenyl)-1-piperazinyl]-2(3H)-benzimidazolone with cis-{[2-(2,4-dichlorophenyl) -2-(1H-imidazol-1-ylmethyl)]-1,3-dioxolan-4-yl}methyl meth-anesulfonate in the presence of sodium hydride furnish the title compounds. 相似文献
13.
Peter Gajdoš Soňa Pavlíková Filip Bureš Alžbeta Krutošíková 《Central European Journal of Chemistry》2005,3(2):311-325
The synthesis and reactions of methyl 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole-5-carboxylate (1a) are described. Upon reaction with methyl iodide, benzyl chloride, or acetic anhydride, this compound gave N-substituted products 1b-d. By hydrolysis of compounds 1a-c, the corresponding acids 2a-c were formed, or by reaction with hydrazine-hydrate, the corresponding carbohydrazides 3a-c were formed. By heating 2-[3-(trifluoromethyl)phenly]-4H-furo[3,2-b]pyrrole-5-carboxylic acid (2a) in acetic anhydride, 4-acetyl-2-[3-(trifluoromethyl)phenyl]furo[3,2-b]pyrrole (4) was formed. By hydrolysis of 4, 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole (5a) was formed, and reactions with methyl iodide or benzyl chloride gave N-substituted products 5b-c. The reaction of 4 with dimethyl butynedioate gave substituted benzo[b]furan 6. Compound 3a reacted with triethyl orthoesters giving 7a-c, which afforded with phosphorus (V) sulphide the corresponding thiones 8a-c. The thiones 8a-c reacted with hydrazine hydrate to form hydrazine derivatives 9a-c. The reaction of triethyl orthoformiate with compounds 9a-c led to furo[2′,3′: 4,5]pyrrolo[1,2-d][1,2,4]triazolo[3,4-f][1,2,4]triazines 10a-c. Hydrazones 11a-c were formed from 3a-c and 5-[3-(trifluoromethyl)phenyl]furan-2-carboxaldehyde. The effect of microwave irradiation on some condensation reactions
was compared with “classical” conditions. The results showed that microwave irradiation shortens the reaction time while affording
comparable yields. 相似文献
14.
The reaction of methyl 2-bromo-6-(trifluoromethyl)-3-pyridinecarboxylate ( 1 ) with methanesulfonamide gave methyl 2-[(methylsulfonyl)amino]-6-(trifluoromethyl)-3-pyridine-carboxylate ( 2 ). Alkylation of compound 2 with methyl iodide followed by cyclization of the resulting methyl 2-[methyl(methylsulfonyl)amino]-6-(trifluoromethyl)-3-pyridinecarboxylate ( 3 ) yielded 1-methyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide ( 4 ). The reaction of compound 4 with α,2,4-trichlorotoluene, methyl bromopropionate, methyl iodide, 3-trifluoromethylphenyl isocyanate, phenyl isocyanate and 2,4-dichloro-5-(2-propynyloxy)phenyl isothiocyanate gave, respectively, 4-[(2,4-dichlorophenyl)methoxy]-1-methyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazine 2,2-dioxide ( 5 ), methyl 2-[[1-methyl-2,2-dioxido-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazin-4-yl]oxy]propanoate ( 6 ), 1,3,3-trimethyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide ( 7 ), 4-hydroxy-1-methyl-7-(trifluoromethyl)-N-[3-(trifluoromethyl)phenyl]-1H-pyrido[2,3-c][1,2]thiazine-3-carboxamide 2,2-dioxide ( 8 ), 4-hydroxy-1-methyl-7-(trifluoromethyl)-N-phenyl-1H-pyrido[2,3-c][1,2]thiazine-3-carboxamide 2,2-dioxide ( 9 ) and N-[2,4-dichloro-5-(2-propynyloxy)phenyl]-4-hydroxy-1-methyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2] thiazine-3-carboxamide 2,2-dioxide ( 10 ). 相似文献
15.
1,3-Dipolar cycloaddition reaction of bis{[4-(3,4-dihydro-(2H)-naphthalen-1-oxo-2-yl)methyl-idenephenyl]oxy}alkanes with nitrilimines (generated in situ by triethylamine dehydrohalogenation of the corresponding hydrazonoyl chlorides) in refluxing dry benzene afforded a mixture
of monocycloadduct and dicycloadduct products in high regioselectivity. On the other hand, reaction of bis{[2-(3,4-dihydro-(2H)-naphthalen-1-oxo-2-yl)methylidenephenyl]oxy}alkanes with nitrilimines gave the corresponding dicycloadducts as the only
isolable regioisomers. 相似文献
16.
George C. Wright 《Journal of heterocyclic chemistry》1976,13(3):601-603
In a study of the synthesis (unsuccessful) of pyrido[3,4-e]-as-triazino-3 (4H)one (6) , the acidification of 2-(3-amino-4-pyridyl)hydrazinecarboxylate hydrochloride (8) unexpectedly gave 1-amino-1H-imidazo[4,5-c]pyridin-2(3H) one hydrochloride (10). The isolation and characterization of 10 has been described. 相似文献
17.
A one-step procedure was developed for the synthesis of 5-acetyl-2-amino-4-aryl-3-cyano-4H-pyrano[3,2-b]indoles involving the three-component reaction of 1-acetylindol-3(2H)-one with aromatic aldehydes and malononitrile in ethanol in the presence of triethylamine as the catalyst. The structure of 5-acetyl-2-amino-4-(4"-chloro-3"-nitrophenyl)-3-cyano-4H-pyrano[3,2-b]indole was established by X-ray diffraction analysis. 相似文献
18.
《Tetrahedron letters》2013,54(48):6427-6429
The reaction between 5-R-6-R1-3-(2-pyridyl)-1,2,4-triazines and benzyne generated in situ in toluene under reflux results in the formation of 10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles 3 in up to 60% yields instead of the expected 3-R-4-R1-1-(2-pyridyl)isoquinolines 2. The crystal structure of product 3c and the proposed mechanism for the formation of 3 are reported. 相似文献
19.
Keigo Kosaka Kazumi Maruyama Haruko Nakamura Masazumi Ikeda 《Journal of heterocyclic chemistry》1991,28(8):1941-1944
Diels-Alder reaction of methyl (E)-3-(1H-imidazol-4-yl)propenoates 2, 3a-c and (E)4-(2-nitroethenyl)-1H-imidazoles 3d,e with 2,3-dimethyl-1,3-butadiene, cyclopentadiene, and cyclohexa-1,3-diene gave the corresponding cycloadducts 6–9 . 相似文献
20.
Ethyl 2-amino-4-methyl-5-(1H-1,2,4-triazol-1-yl)thiophene-3-carboxylate 2, obtained from Gewald reaction of 1-(1H-1,2,4-triazol-1-yl)acetone 1 with ethyl cyanoacetate and sulfur, was transferred into iminophosphorane 3. Further reaction of 3 with aromatic isocyanates gave carbodiimides 4, which were treated subsequently with a secondary amine to give 6-(1H-1,2,4-triazol-1-yl)-thieno[2,3-d]pyrimidin-4(3H)-ones 6 in good yields in the presence of a catalytic amount of sodium ethoxide. 相似文献