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1.
M. M. El’chaninov A. A. Achkasova I. M. El’chaninov 《Russian Journal of General Chemistry》2014,84(9):1697-1700
Three-component reaction of acenaphthenequinone, 9,10-thiophene-2-carbaldehyde and ammonium acetate in glacial acetic acid afforded 2-(2-thienyl)-1H-acenaphtho[1,2-d]imidazole. Its N-methylated product undergoes electrophilic substitution reactions (nitration, bromination, sulfonation, formylation, acylation) in KOH-1-methyl-2-pyrrolidone mixture. Depending on the reaction conditions electrophilic attack occurred at both thiophene ring and acenaphthene fragment. 相似文献
2.
A. A. Aleksandrov M. M. El’chaninov E. V. Illenzeer 《Russian Journal of Organic Chemistry》2013,49(9):1361-1363
The condensation of 2-aminonaphthalen-1-ol with thiophene-2-carbonyl chloride in 1-methylpyrrolidin-2-one gave 2-(2-thienyl)naphtho[2,1-d]oxazole which was brought into electrophilic substitution reactions: nitration, bromination, sulfonation, formylation, and acylation. Depending on the conditions, the attack by electrophile was directed at both thiophene ring and naphthalene fragment in the thienylnaphthooxazole molecule. 相似文献
3.
A. A. Aleksandrov M. M. El’chaninov A. S. Dedeneva 《Russian Journal of General Chemistry》2012,82(7):1263-1266
2-(2-Thienyl)-1(3)H-imidazo{cm[4,5-f]}quinoline was synthesized by the Weidenhagen reaction of quinoline-5,6-diamine with thiophene-2-carbaldehyde. Its methylation in the system KOH-DMSO gave isomeric 1-methyl-2-(2-thienyl)-1H- and 3-methyl-2-(2-thienyl)-3H-imidazo{cm[4,5-f]}quinolines, the latter being the major product. The 3-methyl derivative was subjected to electrophilic substitution reactions (bromination, nitration, formylation, acylation, sulfonation). Depending on the conditions, electrophilic attack was directed at the thiophene or quinoline fragment or both these. 相似文献
4.
E. V. Illenzeer M. M. El’chaninov A. A. Alexandrov 《Russian Journal of General Chemistry》2013,83(1):91-94
The condensation of 1,2-dimethylbenzimidazole with thiophene-2-aldehyde in the presence of fused zinc chloride results in 1-methyl-2-[β-(2-thienyl)vinylene]-1H-benzimidazole. Its electrophilic substitution reactions (nitration, bromination, sulfonation, formylation, acylation) were studied. All the reactions occur in the 5-position of the thiophene ring. Only in the case of bromination in dichloroethane 5′,5(6)-dibromo-derivative was obtained. Data of the quantum-chemical calculations of the total positive charge on the carbon atoms of the protonated molecules of thienylbenzimidazoles including the vinylene group and without it are reported. 相似文献
5.
E. V. Vlasova A. A. Aleksandrov M. M. Elchaninov A. A. Milov B. S. Lukyanov 《Chemistry of Heterocyclic Compounds》2011,47(6):684-689
5-(2-Furyl)-1-methyl-1H- and 1-methyl-5-(2-thienyl)-1H-imidazoles were synthesized. The electronwithdrawing effect of the
5- and 2-imidazole substituents on the furan ring was studied by 1H NMR spectroscopy and quantum-chemical calculations. Some electrophilic substitution reactions were investigated (nitration,
bromination, sulfonation, hydroxymethylation, formylation, and acylation). In some cases, depending on the reaction conditions,
both the furan and thiophene ring and the imidazole fragment undergo electrophilic attack. 相似文献
6.
Oxidation of N-(1-methylbenzimidazol-5-yl)thiophene-2-carbothioamide with potassium ferricyanide in an alkaline medium by Jacobson’s method afforded 2-(thien-2-yl)-6-methyl-6H-imidazo[4,5-g][1,3]benzothiazole. The latter enters into the electrophilic substitution reaction (nitration, bromination, formylation, acylation) exclusively at the position 5 of the thiophene ring. Characteristic reactions of nucleophilic substitution occurred at the imidazole ring. Quaternization with methyl iodide in benzene furnished the corresponding quaternary salt, whereas the Chichibabin amination with an excess of sodium amide in xylene gave negative result. 相似文献
7.
1-Methyl-2-(thiophen-3-yl)-1H-benzimidazole was synthesized by the Weidenhagen reaction, followed by N-methylation. Electrophilic substitution reactions of the title compound, in particular nitration, bromination, sulfonation, formylation, and acylation, were studied. The formylation and acylation in polyphosphoric acid afforded mixtures of 2- and 5-substituted isomers at the thiophene ring. The nitration of 1-methyl-2-(thiophen-3-yl)-1H-benzimidazole involved the thiophene ring or both thiophene and benzene fragments, depending on the conditions. Steric arrangement of the heterocycles in the 1-methyl-2-(thiophen-3-yl)-1H-benzimidazole molecule was analyzed by quantum chemical calculations. 相似文献
8.
A. A. Aleksandrov A. S. Dedeneva M. M. El’chaninov 《Russian Journal of Organic Chemistry》2011,47(5):710-713
By condensation of 1-amino-2-hydroxynaphthalene with furoyl chloride in 1-methyl-2-pyrrolidone 2-(2-furyl)naphtho[1,2-d]oxazole
was synthesized and brought into electrophylic substitution reactions: nitration, bromination, sulfonation, formylation, and
acylation. The substituent commonly was introduced into the position 5 of the furan ring, but at the nitration and bromination electrophilic attack was directed both at the furan ring and the
naphthalene fragment. 相似文献
9.
A. A. Aleksandrov E. V. Vlasova M. M. El’chaninov 《Russian Journal of Organic Chemistry》2010,46(6):898-902
Condensation of o-aminophenol with furoyl and thenoyl chlorides in 1-methylpyrrolidin-2-one gave, respectively, 2-(2-furyl)- and 2-(2-thienyl)-1,3-benzoxazoles
in which the furan and thiophene rings showed no acidophobic properties. Reactions of 2-(2-furyl)- and 2-(2-thienyl)-1,3-benzoxazoles
with electrophilic reagents (acylation, bromination, nitration, and sulfonation) afforded products of hydrogen replacement
in both hetaryl and benzene rings, depending on the conditions. 相似文献
10.
A. A. Alexandrov E. A. Prorervo M. M. El’chaninov 《Russian Journal of Organic Chemistry》2016,52(5):727-729
Reaction of acenaphthylene-1,2-dione and furan-2-carbaldehyde in ethanol with an excess of ammonia water solution afforded 2-(furan-2-yl)acenaphtho[1,2-d]oxazole whose reactions of electrophilic substitution (nitration, bromination, hydroxymethylation, formylation, acylation) were examined. Notwithstanding the reaction conditions the electrophilic attack was directed on the furan ring. 相似文献
11.
E. V. Illenzeer A. A. Aleksandrov M. M. El’chaninov 《Russian Journal of Organic Chemistry》2012,48(7):968-971
2-(2-Furyl)-5,6-dihydro-1(3)H-acenaphtho[4,5-d]imidazole was synthesized by the Weidenhagen reaction of acenaphthene-4,5-diamine with furfural. Alkylation of the title compound with methyl iodide in KOH-DMSO gave isomeric 1- and 3-methyl derivative, the latter being the major product. 2-(2-Furyl)-3-methyl-5,6-dihydro-3H-acenaphtho[4,5-d]imidazole was subjected to electrophilic substitution reactions (bromination, nitration, formylation, acylation, and sulfonation. Depending on the conditions, electrophilic attack was directed at the furan ring or acenaphthene fragment or both these. 相似文献
12.
In the electrophilic substitution reactions (bromination, nitration, diazo coupling, Sommelet formylation, and aminomethylation) of 2-carbomethoxy-5-hydroxy-benzofuran substituents primarily enter the 4 position. 相似文献
13.
N-(1-Naphthyl)furan-2-carboxamide was synthesized by the coupling of naphthalen-1-amine with furan-2-carbonyl chloride in propan-2-ol and then treated with excess P2S5 in anhydrous toluene to obtain the corresponding thioamide. The latter was oxidized with potassium ferricyanide in an alkaline medium by the Jakobson procedure to synthesize 2-(furan-2-yl)benzo[e][1,3]benzothiazole which was subjected to electrophilic substitution reactions: nitration, bromination, formylation, and acylation. 相似文献
14.
E. B. Melnikova M. M. Elchaninov A. A. Milov B. S. Lukyanov 《Chemistry of Heterocyclic Compounds》2008,44(9):1070-1076
The electrophilic reactions (nitration, bromination, hydroxymethylation, formylation, acylation) and radical substitution
reactions (nitration, arylation) of 2-(2-furyl)benzothiazole have been studied. It was found that all of the reactions occur
at position 5 of the furan ring. Only nitration in PPA gave the 5',6-dinitro derivative. Quantum-chemical calculation data
for the electron density distribution in the neutral and protonated 2-(2-furyl)benzothiazole molecules are given.
Dedicated to Boris Aleksandrovich Trofimov on his 70th jubilee.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1331–1338, September, 2008. 相似文献
15.
Condensation of ortho-aminothiophenol with 2-thenoyl chloride in 1-methyl-2-pyrrolidone was used to synthesize 2-(2′-thienyl)benzothiazole. Its
reactions of electrophilic (nitration, bromination, oxymethylation, formylation, acylation) and radical (nitration, arylation)
substitution were studied. 相似文献
16.
A. A. Aleksandrov A. S. Dedeneva E. V. Vlasova M. M. El’chaninov 《Russian Journal of Organic Chemistry》2011,47(1):120-123
2-(2-Furyl)-1(3)H-imidazo[4,5-f]quinoline was synthesized by the Weidenhagen reaction of quinoline-5,6-diamine with furfural. Its alkylation with methyl iodide in the system KOH-DMSO gave two isomeric N-methyl derivatives, 2-(2-furyl)-1-methyl-1H- and 2-(2-furyl)-3-methyl-3H-imidazo[4,5-f]quinolines, the latter prevailing. 2-(2-Furyl)-3-methyl-3H-imidazo[4,5-f]quinoline was brought into electrophilic substitution reactions: bromination, nitration, formylation, acylation, sulfonation. Depending on the reaction conditions, electrophilic attack could be directed at both furan ring and quinoline fragment. 相似文献
17.
E. V. Vlasova A. A. Aleksandrov M. M. El’chaninov 《Russian Journal of Applied Chemistry》2010,83(6):1027-1031
2-Phenyl-5-(2-furyl)- and 2-phenyl-5-(2-thienyl)imidazoles were synthesized by condensation of 2-furoylmethyl and 2-thenoylmethyl
acetates with benzaldehyde under the conditions of Weidenhagen reaction. The products were converted to N-methyl derivatives in the KOH-acetone system. The electrophilic substitution reactions of the products (acylation, bromination,
nitration, sulfonation, hydroxymethylation) were studied. 相似文献
18.
N. N. Bychikhina V. A. Azimov L. N. Yakhontov 《Chemistry of Heterocyclic Compounds》1982,18(3):268-271
The electrophilic substitution reactions (nitration, bromination, acylation, and the Mannich and Vilsmeier reactions) of 1-benzyl-6-methoxy-7-cyano-5-azaindole and the nitration and Vilsmeier reaction of 6-hydroxy-5-azaindoline were studied.See [1] for Communication 60.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 356–360, March, 1982. 相似文献
19.
2-(2-Furyl)-1H-naphto[2,3-d]imidazole was synthesised by interaction of 2,3-diaminonaphtalene with furfural in the conditions of Weidenhagen reaction. At its N-methylation in the KOH-DMSO system the 1-methyl-2-(2-furyl)-1H-naphto[2,3-d]imidazole was obtained, which we subjected to reactions of electrophilic substitution (nitration, bromination, sulfonation, formylation, and acylation). This compound possesses a specific reactivity: all reactions, as a rule, proceed at the naphthalene scaffold while the furan ring is not involved. 相似文献
20.
Salamatina G. V. Aleksandrov A. A. El’chaninov M. M. 《Russian Journal of General Chemistry》2011,81(8):1720-1725
2-(1′-Methyl-2′-pyrrolyl)-1H-phenanthro[9,10-d]imidazole was synthesized by heating 9,10-phenanthrenequinone and 1-methyl-2-pyrrolecarboxaldehyde in glacial acetic acid
in the presence of ammonium acetate. The reactions of electrophilic substitution (nitration, bromination, sulfonation, formylation,
acylation) were studied for the product of its N-methylation in the KOH-DMSO medium. The electrophilic attack was found to
affect exclusively the pyrrole ring. 相似文献