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1.
D. A. Skladchikov A. A. Fatykhov R. R. Gataullin 《Russian Journal of Organic Chemistry》2014,50(1):48-53
7-Bromo-, 7-phenylethynyl-, 7-azido-, 7-nitro-, and 5,7-dinitro-substituted N-acetyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles have been synthesized starting from anilines and 3-chlorocyclopentene. The NMR spectra of N-acetyl-7-nitro-1,3a,4,8b-tetrahydrocyclopenta[b]indoles displayed no signal doubling typical of the other 7-substituted derivatives. 相似文献
2.
N. A. Likhacheva A. A. Korlyukov R. R. Gataullin 《Russian Journal of Organic Chemistry》2009,45(3):394-398
Stereoisomeric 3-acetoxy-5-methoxy-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indoles differing by the configuration of the C3 atom were synthesized. The reaction of N-acetyl-6-(cyclopent-2-en-1-yl)-2-methoxyaniline with 50% hydrogen peroxide in the presence of Na2WO4-H3PO4 in AcOH gave (3RS,3aRS,8bSR)-N-acetyl-3-hydroxy-5-methoxy-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole which was converted into the corresponding 3-O-acetyl derivative by treatment with acetic anhydride in pyridine. N-Acetyl-6-(cyclopent-2-en-1-yl)-2-methoxyaniline reacted with iodine in methylene chloride in the presence of NaHCO3 to produce (3SR,3aRS,8bSR)-3-acetoxy-5-methoxy-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole which was subjected to acetylation at the nitrogen atom by reaction with acetic anhydride. The structure of (3RS,3aRS,8bSR)-N-acetyl-3-hydroxy-5-methyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole was proved by X-ray analysis.
Original Russian Text ? N.A. Likhacheva, A.A. Korlyukov, R.R. Gataullin, 2009, published in Zhurnal Organicheskoi Khimii,
2009, Vol. 45, No. 3, pp. 406–409. 相似文献
3.
R. R. Gataullin T. V. Kazhanova F. F. Minnigulov A. A. Fatykhov L. V. Spirikhin I. B. Abdrakhmanov 《Russian Chemical Bulletin》2000,49(10):1767-1770
When reacting with I2, 2-(cyclopent-2-enyl)anilines undergo cyclization into 3-iodo-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indoles in high yields. The minor reaction products were 3,5- or 3,7-diiodoindolines. Ammonolysis of 3-iodo-5-methyl-1,2,3,3a,4,8b-hexahydro-cyclopenta[b]indole or itsN-chloroacetyl derivative results in 3-amino-5-methyl-1,2,3,3a,48b-hexahydro- and 5-methyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles.
Published inIzvestiya Akademii Nauk. Seriya Khimischeskaya, No. 10, pp. 1789–1793, October, 2000. 相似文献
4.
D. A. Skladchikov K. Yu. Suponitskii I. B. Abdrakhmanov R. R. Gataullin 《Russian Journal of Organic Chemistry》2012,48(7):957-967
Heating of 4-acyl-3-iodo-7-methyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indoles in piperidine gave 4-acyl-7-methyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles which were oxidized with KMnO4 to obtain the corresponding 4-acyl-7-methyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole-1,2-diols. Oxidation of 4-acyl-7-methyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles at the olefinic double bond with hydrogen peroxide in acetonitrile in the presence of formic acid afforded stereoisomeric epoxides with cis and trans orientation of the nitrogen-containing and oxirane rings. Nitration with a mixture of ammonium nitrate and trifluoroacetic anhydride produced 5-nitro derivatives. The structure of 1-{(1aR*,1bR*,6bS*,7aS*)-5-methyl-1a,1b,2,6b,7,7ahexahydrooxireno[4,5]cyclopenta[1,2-b]indol-2-yl}ethanone was determined by X-ray analysis. 相似文献
5.
R. R. Gataullin N. A. Likhacheva K. Yu. Suponitskii I. B. Abdrakhmanov 《Russian Journal of Organic Chemistry》2007,43(9):1310-1321
N-Acyl-2-(cyclohex-2-en-1-yl)anilines react with molecular iodine to give the corresponding N-acyl-1-iodo-1,2,3,4,4a,9a-hexahydrocarbazoles which undergo isomerization into 1-R-2a,3,4,5,5a,10a-hexahydro[1,3]oxazolo[5,4,3-j,k]carbazol-10-ium iodides; no isomerization occurs with N-acetyl-3-iodo1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole. The reaction of N-p-tolylsulfonyl-3,4,4a,9a-tetrahydrocarbazoles with hydrogen peroxide leads to the formation of a single 1,2-epoxy derivative
with trans orientation of the nitrogen-and oxygen-containing rings. N-p-Tolylsulfonyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles give rise to the corresponding 2,3-epoxy derivatives with both trans and cis orientation of the dihydropyrrole and oxirane fragments. The resulting epoxides undergo trans-opening with formation of N-p-tolylsulfonyl-1-hydroxy-2-methoxy-1,2,3,4,4a,9a-hexahydrocarbazoles and N-p-tolylsulfonyl-3-hydroxy-2-methoxy-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indoles on heating in methanol in the presence of KU-2 cation exchanger. Mutual orientation of the oxirane and nitrogen-containing
rings in the epoxides derived from cyclopenta[b]-indoles was proved by X-ray analysis.
Original Russian Text ? R.R. Gataullin, N.A. Likhacheva, K.Yu. Suponitskii, I.B. Abdrakhmanov, 2007, published in Zhurnal
Organicheskoi Khimii, 2007, Vol. 43, No. 9, pp. 1316–1326.
For communication VII, see [1]. 相似文献
6.
The reactions of N-methylsulfonyl-and N-(p-tolylsulfonyl)-2-(cyclopent-1-en-1-yl)-6-methylaniline with molecular bromine in the presence of potassium thiocyanate gave N-methylsulfonyl-and N-(ptolylsulfonyl)-2-(5-isothiocyanatocyclopent-1-en-1-yl)-6-methylanilines. N-Methylsulfonyl-2-(cyclopent-1-en-1-yl)-6-methylaniline reacted with bromine in methanol in the presence of NaHCO3 or with CuBr2 in MeOH to afford N-methylsulfonyl-2-(5-methoxycyclopent-1-en-1-yl)-6-methylaniline. The reaction of N-methylsulfonyl-2-(5-isothiocyanatocyclopent-1-en-1-yl)-6-methylaniline with diethylamine led to the formation of N-methylsulfonyl-2-{5-[diethylamino(thioxo)methyl]aminocyclopent-1-en-1-yl}-6-methylaniline which was converted into 5-methyl-4-methylsulfonyl-2,3,3a,4-tetrahydrocyclopenta[b]indole by heating with potassium hydroxide. 相似文献
7.
R. R. Gataullin R. R. Ishberdina O. V. Shitikova F. F. Minnigulov L. V. Spirikhin I. B. Abdrakhmanov 《Chemistry of Heterocyclic Compounds》2006,42(8):1025-1031
Halocyclization of mesylates or tosylates of 2-(cycloalk-2-en-1-yl)anilines gives N-methanesulfonyl-or N-toluenesulfonyl-1-halo-1,2,3,4,4a,9a-hexahydrocarbazoles,
heating of which in DMF at 160°C or in piperidine at 110°C leads to 4,4a,9,9a-tetrahydro-3H-carbazoles. Heating N-methanesulfonyl-1-iodo-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole
in DMF at 180—200°C gives 1,3a,4,9b-tetrahydrocyclopenta[b]indole, while in the presence of an ortho-methyl substituent the
dehydroiodination reaction proceeds in piperidine at 110°C in high yield. The effect of the nature of the ortho substituent
of N-methyl-1-iodo-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole on the conformational equilibrium of the cyclopentane ring has
been established by 1H NMR spectroscopy.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1184–1190, August, 2006. 相似文献
8.
R. R. Gataullin R. R. Ishberdina A. V. Antipin K. Yu. Suponitskii N. N. Kabal’nova O. V. Shitikova L. V. Spirikhin M. Yu. Antipin I. B. Abdrakhmanov 《Chemistry of Heterocyclic Compounds》2006,42(9):1130-1136
In reaction with dimethyldioxirane N-mesyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles and N-mesyl-3,3,4a,9a-tetrahydrocarbazoles
mostly form the trans-epoxide. The reaction with molecular bromine leads to the product from halogenation in the aromatic
ring, i.e., the corresponding N-mesyl-7-bromo-1,3a,4,8b-tetrahydrocyclopenta[b]indole or N-mesyl-6-bromo-3,4,4a,9a-tetrahydrocarbazole.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1306–1313, September, 2006. 相似文献
9.
F. A. Gimalova E. M. Minnibaeva M. S. Miftakhov 《Russian Journal of Organic Chemistry》2007,43(11):1651-1655
2,3,5-Trichloro-4,4-dimethoxy-5-(2-methylfuran-3-yl)cyclopent-2-en-1-one reacted with secondary amines to give unusual AdNE-substitution-fragmentation products, 5-[(1Z,2E)-1-acetyl-3-dialkylaminoprop-2-en-1-ylidene]-3-dialkylamino-2-chloro-4,4-dimethoxycyclopent-2-en-1-ones. 相似文献
10.
A. M. Borisov N. A. Kamanina A. V. Velikorodov 《Russian Journal of Organic Chemistry》2007,43(3):414-416
N,N′-Bis(methoxycarbonyl)-p-benzoquinone diimine reacted with 4-(cyclohex-1-en-1-yl)-and 4-(cyclopent-1-en-1-yl)morpholines in methylene chloride at room temperature to give morpholino-substituted cyclohexane-and cyclopentane-fused indole derivatives. Heating of the latter in boiling 10% hydrochloric acid led to the formation of methyl 6-(methoxycarbonylamino)-1,2,3,4,4a,9a-hexahydro-9H-carbazole-9-carboxylate and methyl 7-(methoxycarbonylamino)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole-4-carboxylate, respectively. The reaction of N,N′-bis(methoxycarbonyl)-p-benzoquinone diimine with 4-benzylaminopent-3-en-2-one in CH2Cl2 in the presence of BF3·Et2O on heating gave methyl 3-acetyl-2-methyl-(5-methoxy-carbonylamino)-1H-indole-1-carboxylate. 相似文献
11.
R. R. Gataullin D. A. Skladchikov A. A. Fatykhov 《Russian Journal of Organic Chemistry》2013,49(2):272-275
The nitration of N-acyl-7-methyl-1,3a,4,8b-tetrahydrocyclopenta[b]indole with a mixture NH4NO3-(CF3CO)2O afforded 5-nitro derivatives whose reduction with Fe(OH)2 in H2O led to the formation of 5-amino derivatives. The oxidation of the 5-amino derivatives with Fremy’s salt gave the corresponding indoloquinones. 相似文献
12.
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
13.
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
14.
Reactions of 3-[(2-bromoprop-2-en-1-yl)sulfanyl]-5H-[1,2,4]triazino[5,6-b]indole with bromine and of 3-[(2-methylprop-2-en-1-yl)sulfanyl]-5H-[1,2,4]triazino[5,6-b]indole with iodine and bromine afforded 3-halomethyl-10H-[1,3]thiazolo[3′,2′: 2,3][1,2,4]triazino[5,6-b]indol-4-ium halides whose structures were determined by 1H NMR and X-ray analysis. 相似文献
15.
R. R. Gataullin I. S. Afon'kin A. A. Fatykhov L. V. Spirikhin I. B. Abdrakhmanov 《Russian Chemical Bulletin》1990,49(1):122-124
The reaction ofN-acetyl-2-(cyclohex-1-enyl)aniline with Br2 orN-bromsuccinimide at 20°C is accompanied by intramolecular cyclization to give brominated 3,1-benzoxazines or 4-acetyl-(3-bromo-5-methyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 118–120, January, 2000. 相似文献
16.
R. R. Gataullin I. S. Afon'kin A. A. Fatykhov L. V. Spirikhin I. B. Abdrakhmanov 《Russian Chemical Bulletin》2000,49(1):122-124
The reaction ofN-acetyl-2-(cyclohex-1-enyl)aniline with Br2 orN-bromsuccinimide at 20°C is accompanied by intramolecular cyclization to give brominated 3,1-benzoxazines or 4-acetyl-(3-bromo-5-methyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 118–120, January, 2000. 相似文献
17.
N. A. Likhacheva A. A. Fatykhov I. B. Abdrakhmanov R. R. Gataullin 《Russian Journal of Organic Chemistry》2007,43(9):1305-1309
Hydroxymercuration-demercuration of N-p-tolysulfonyl-4,4a,9,9a-tetrahydro-3H-carbazoles and N-p-tolyl(or methyl)sulfonyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles leads to the formation of the corresponding N-p-tolylsulfonyl-2,3,4,4a,9,9a-hexahydro-1H-carbazol-2-ols and N-p-tolyl(or methyl)sulfonyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-2-ols. The latter are oxidized to 2-oxo derivatives with potassium dichromate. The oxidation of 2-methoxy-8-methyl-N-p-tolylsulfonyl-2,3,4,4a,9,9a-hexahydro-1H-carbazol-1-ol under analogous conditions gives 2-methoxy-8-methyl-N-p-tolysulfonyl-2,3,4,4a,9,9a-hexahydro-1H-carbazol-1-one. 相似文献
18.
The reaction of N-(1-methylbut-2-en-1-yl)-2-iodaniline with Ac2O or ClCH2C(O)Cl results in a mixture of syn- and anti-atropisomers of N-acetyl- and N-chloroacetyl-N-(1-methylbut-2-en-1-yl)-2-iodaniline in a ratio of 1:1. Ozonolysis of the latter followed by reduction with dimethyl sulfide in CH2Cl2 gives rise to the atropisomers mixture of 2-[N-(chloroacetyl)-N-(2-iodophenyl)]aminopropanal in a ratio of 1:3. When heated in boiling benzene, the mixture of atropoisomeric aldehydes reacts with triphenylphosphine to afford a mixture of 2-[(N-acetyl)-N-(2-iodophenyl)]aminopropanal atropisomers in 1:3 ratio. 相似文献
19.
Guliya G. Bizhanova Kyrill Yu. Suponitsky Yulia V. Vakhitova Rail R. Gataullin 《Tetrahedron》2017,73(2):109-115
We synthesized methyl ester of N-(1-methylbut-2-en-1-yl)-N-phenylglycine which underwent acid catalyzed aromatic amino Claisen rearrangement to provide methyl-N-[2-(1-methylbut-2-en-1-yl)phenyl]glycinate. A mixture of syn- and anti-atropisomeric methyl-N-acetyl-N-[4-methyl-2-(1-methylbut-2-en-1-yl)phenyl]glycinates was obtained either by the reaction of this ester with acetyl bromide or by the reaction of the sodium salt of N-acetyl-2-(1-methylbut-2-en-1-yl)-4-methylaniline with methyl bromoacetate. Upon saponification of the synthesized ester mixture the syn-atropisomer of N-acetyl-N-[4-methyl-2-(1-methylbut-2-en-1-yl)phenyl]glycine was isolated by fractional crystallization. Treatment of the obtained acids with acetic anhydride, ethyl chloroformate, dicyclohexylcarbodiimide or isopropenylacetate leads to compounds of 4,5-dihydro-3aH-methano[1,3]oxazolo[3,2-a]quinolin-2-one structure. 相似文献
20.
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