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1.
S. Yu. Ryabova A. S. Shashkov L. M. Alekseeva E. A. Lisitsa V. G. Granik 《Russian Chemical Bulletin》2007,56(8):1595-1602
The reactions of 3-[N-chloracetylamino-N-(4-nitrophenyl)]-2-formylindole (1a) with 2-(N, N-dialkylamino)ethylamines afford complex condensation products 7b,c consisting of two similar but not identical diazepinoindole fragments. For the reaction of compound 1a with 3-(N,N-diethylamino)propylamine, the process occurs in a different manner, and the predominant product is 4-ethylaminopropyl-1-(4-nitrophenyl)-2-oxo-1,2,3,4,5,6-hexahydro[1,4]diazepino[6,5-b]indole hydrocloride (14). Two routes of these unexpected transformations were proposed. The structures of the synthesized products were proved by
the 1sH and 13C NMR, HMBC, and HSQC (direct proton-carbon correlation) spectra.
Dedicated to Academician V. A. Tartakovsky on the occasion of his 75th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1536–1542, August, 2007. 相似文献
2.
N. L. Agarwal S. Ghosh A. K. Tripathi C. K. Atal 《Journal of heterocyclic chemistry》1984,21(2):509-512
The reaction of 2-N-(acetylanilino)-3-chloro-1,4-naphthoquinone ( 2 ) with bifunctional aromatic amines afforded angular heterocycles 6 and 7 . Reductive acetylation of 7 provided o-acyl 9 and O,N-diacyl 10 derivatives depending upon the reaction conditions. The ir, uv, pmr and mass spectral data are also presented. 相似文献
3.
Ivana Bradiaková Tatiana Ďurčeková Naďa Prónayová Anton Gatial Alžbeta Krutošíková 《Chemical Papers》2009,63(5):586-591
2-[3-(Trifluoromethyl)phenyl]-4,5-dihydrofuro[3,2-c]pyridin-4-one (I) was prepared by a three-step synthesis. Its reaction with phosphorus sulfide rendered thione II which was methylated to 2-[3-(Trifluoromethyl)phenyl]-4-methylsulfanylfuro[3,2-c]pyridine (III). 5-Methyl-2-[3-(trifluoromethyl)phenyl]-4,5-dihydrofuro[3,2-c]pyridin-4-one (IV) was obtained by the reaction of I with methyl iodide in PTC conditions. The chlorine atom in derivate V was replaced with heterocyclic secondary amines via nucleophilic substitution and 4-substituted furopyridines VIa and VIb were thus prepared. 2-[3-(Trifluoromethyl)phenyl]furo[3,2-c]pyridine-4-carboxylic acid (VII) was obtained by hydrolysis of the corresponding carbonitrile Va. 相似文献
4.
Addition of HCl to 2-amino-3-(4-methyl-3-oxopentynyl)-1,4-naphthoquinone in CHCl3 at 20 °C is followed by its cyclization to 4-chloro-2-isopropylbenzo[g]quinoline-5,10-dione. Chlorine atom in this compound can be easily replaced by dialkylamino group upon treatment with secondary
amines. 4-Dialkylamino-2-isopropylbenzo[g]quinoline-5,10-dione is also formed by the direct reaction of the starting ketone with secondary amines. Syntheses of 2-amino-3-(4-methyl-3-oxopentynyl)-1,4-naphthoquinone
from 2-bromo-and 2-amino-3-iodo-1,4-naphthoquinones are also described.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2381–2385, December, 2007. 相似文献
5.
N-(3-Azido-2-nitroxypropyl)-N-alkylnitramines andN-(2,3-diazidopropyl)-N-alkylnitramines were prepared by nitration and azidation ofN-alkyl-N-(2-hydroxy-3-chloropropyl)sulfamates andN-(3-azido-2-hydroxypropyl)-N-alkylsulfamates.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 206–208, January, 1999. 相似文献
6.
V. P. Glazunov D. V. Berdyshev A. Ya. Yakubovskaya N. D. Pokhilo 《Russian Chemical Bulletin》2006,55(10):1729-1736
The molecular structures of various conformers of 2-hydroxy-1,4-naphthoquinone; 3-(alk-1-enyl)-2-hydroxy-1,4-naphthoquinones;
2,5,8-trihydroxy-1,4-naphthoquinone; and 3-(alk-1-enyl)-2,5,8-trihydroxy-1,4-naphthoquinones were studied by density functional
theory (B3LYP/6-31(d), B3LYP/6-31(d, p)) and ab initio (MP2/6-31G, MP2/6-31(d)) methods. The strengths of the intramolecular hydrogen bonds formed by the β-hydroxy group with the
O atom at C(1) and with the double bond π-electrons of the alkenyl substituents in the quinonoid rings were estimated. The
compounds studied mainly exist as rotamers with the former-type hydrogen bonds. The splitting of the quinonoid bands of the
stretching vibrations of the β-hydroxy group in the IR spectra of 3-(alk-1-enyl)-2-hydroxy-1,4-naphthoquinones and 3-(alk-1-enyl)-2,5,8-trihydroxy-1,4-naphthoquinones
in hexane solutions is due to the existence of rotamers formed upon internal rotation of the alkenyl substituent.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1667–1673, October, 2006. 相似文献
7.
D. N. Pelageev M. N. Panchenko N. D. Pokhilo V. A. Denisenko V. F. Anufriev 《Chemistry of Natural Compounds》2008,44(6):719-723
5,8-Dihydroxy-2,3,6-trimethoxy-7-ethyl-1,4-naphthoquinone (1) was used to synthesize in high yield 5,8-dihydroxy-7(1′-hydroxyethyl)-2,3,6-trimethoxy-1,4-naphthoquinone (lomazarin, 3), a pigment from Lomandra hastilis. Alkaline hydrolysis of lomazarin produced mainly 5,6,8-trihydroxy-2,3-dimethoxy-1,4-naphthoquinone (9) through a retro-aldol decomposition of the 6-keto-form of 5,6,8-trihydroxy-7(1′-hydroxyethyl)-2,3-dimethoxy-1,4-naphthoquinone
(13b) formed during the reaction. 2,5,8-Trihydroxy-7(1′-hydroxyethyl)-3,6-dimethoxy-1,4-naphthoquinone (norlomazarin, 4a), a pigment of L. hastilis, and its 3,5,8-trihydroxy-7(1′-hydroxyethyl)-2,6-dimethoxy isomer 4b were formed as a difficultly separable mixture in addition to quinone 9.
Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 581–584, November–December, 2008. 相似文献
8.
Reaction of 4-(N,N-Dimethylaminophenyl)magnesium Bromide with Palladium Tetrakis(triphenylphosphine)
Tomashevskii A. A. Sokolov V. V. Potekhin A. A. 《Russian Journal of Organic Chemistry》2003,39(2):226-234
The influence of reaction conditions on catalyzed by Pd(PPh3)4 cross-coupling of 4-N,N-dimethylaminophenylmagnesium bromide with 4-bromobenzonitrile in tetrahydrofuran was investigated. The yield of the product of the catalytic process, 4-N,N-dimethylamino-4'-cyanobiphenyl, and of the main product of noncatalytic process, 4-N,N-dimethylaminophenyl 4'-bromophenyl ketone, is mainly governed by the order of introduction of reagents and catalyst into the reaction zone. Experimental observations and analysis of side products suggested conclusions on the processes resulting in deactivation of the catalyst. 相似文献
9.
Galina Temtsin-Krayz Alexander I. Shames Shmuel Bittner 《Research on Chemical Intermediates》2003,29(3):325-333
EPR spectroscopy was used to assess the radicals produced upon basic decomposition of N,N-bis-(3-chloro-1,4-naphthoquinon-2-yl) amine (BClNQA). Three radicals have been trapped and identified: N-bis(3-chloro-1,4-naphthoquinone) hydrazine radical (6), 2-hydroxy-3-chloro-1,4-naphthoquinone anion radical (9) and 2-amino-3-chloro-1,4-naphthoquinone radical (8). The probable reaction mechanism, the structure of intermediates as well as the reaction profile are discussed. 相似文献
10.
A. L. Romanyuk B. L. Litvin N. I. Ganushchak 《Russian Journal of General Chemistry》2002,72(2):280-282
2-Hydroxy-3-(benzotriazol-1-yl)-1,4-naphthoquinone reacts with o-phenylenediamine and 4-chloro-2-aminophenol to give cyclization products: 5-oxo-6-(benzotriazol-1-yl)-5,6H-benzo[a]phenazine and 5-oxo-6-(benzotriazol-1-yl)-10-chlorobenzo[a]phenoxazine; the reaction with aniline yields the quaternary anilinium salt, and benzoyl chloride and benzenesulfonyl chloride acylate the nitrogen atom of the benzotriazolyl moiety. 相似文献
11.
Ippolito Antonini Francesco Claudi Gloria Cristalli Mario Grifantini Sante Martelli 《Journal of heterocyclic chemistry》1980,17(1):181-185
The course of the thermal, acid-catalysed and iodide-catalysed decomposition of 2-amino-3-(2′,2′-dimethylaziridino)-1,4-naphthoquinone (III) was investigated. Thermal and iodide-catalysed decompositions gave mainly 2,3-diamino-1,4-naphthoquinone (VI) and 2-amino-3-(2′-methylallylamino)-1,4-naphthoquinone (V) together with low amounts of 2,2-dimethyl-1,2,3,4,5,10-hexahydrobenzo[g]quinoxaline (IV) and 2-isopropyl-1H-naphthoimid-azole-4,9-dione (VII). The acid catalysed isomerization of the aziridinonaphthoquinone III with halohydric acids or with acetic acid readily gave the opening of the aziridine ring; the corresponding salts of 2-amino-3-(2′-haloisobutylamino)-1,4-naphthoquinones (VIIIa-c) and 2-amino-3-(2′-acetoxyisobutylamino)-1,4-naphthoqunone (X) were formed by cleavage of the carbon-nitrogen bond at the substituted carbon atom. Hypotheses on the mechanism of these reactions are given. 相似文献
12.
Photochemical transformations of 2-arylamino-1-(4-tert-butylphenoxy)-9,10-anthraquinones involve migration of thetert-butylphenyl group either to theperi-located carbonyl oxygen to give 2-arylamino-9-(4-tert-butylphenoxy)-1,10-anthraquinones or to the nitrogen atom to give 2-aryl(4-tert-butylphenyl)amino-1-hydroxy-9,10-anthraquinones (typical products of the Smiles rearrangement).
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2519–2522, December, 1998. 相似文献
13.
When 4,6,7-trichloro-5-hydroxy-2-(2-pyrimidylamino)- 2,3-dihydrobenzo[b]furan reacted with phenyliodoso diacetate, an unexpected oxidative recyclization was observed to give 3-(3,5,6-trichloro-1,4-benzoquinon-2-yl)imidazo[1,2-a]pyrimidine. 2-[N-2-(3,5,6-Trichloro-1,4-benzoquinon-2-yl)ethenylamino]pyrimidine is the intermediate product in the conversion. 相似文献
14.
Giulia Menozzi Luisa Mosti Pietro Schenone Sergio Cafaggi 《Journal of heterocyclic chemistry》1982,19(4):937-939
The 1,4-cycloaddition of sulfene to N,N-disubstituted (E)-4-aminomethylene-3,4-dihydro-1-benzoxepin-5(2H)-ones gave, generally in excellent yield, N,N-disubstituted 4-amino-3,4,5,6-tetrahydro-1,2-oxathiino-[5,6-d)-1-benzoxepin 2,2-dioxides, which are derivatives of the new heterocyclic system 1,2-oxathiino[5,6-d]-1-benzoxepin. This reaction did not occur only with the N,N-diphenylenaminone. 相似文献
15.
Ayecik KAMAZ 《Turkish Journal of Chemistry》2021,45(2):475
A series of NH-substituted-1,4-quinones, possessing one, two, three or not chlorine, were synthesized by the reaction between different quinones (p-chloranil (1), p-toluquinone (2), or 2,3-dichloro-1,4-naphthoquinone (3)) and (-)-cis-myrtanylamine (5) via nucleophilic reactions. Moreover, 2-bromo-1,4-naphthoquinone (4) was reacted with 2-(methylthio)ethylamine (11) to produce amino-substituted naphthoquinones (12 and 13), bearing with bromine and not bromine. In addition, 2-bromo-1,4-naphthoquinone (4) was reacted with 4′-aminodibenzo-18-crown-6 (14) and 4′-aminobenzo-18-crown-6 (16) to yield crown-containing 1,4-naphthoquinones (15 and 17), respectively. New compounds were characterized, providing 1H NMR, 13C NMR, FTIR, MS-ESI, UV/Vis and elemental analysis. 相似文献
16.
Gaetano Bignardi Luisa Mosti Pietro Schenone Giulia Menozzi 《Journal of heterocyclic chemistry》1977,14(6):1023-1028
The 1,4-cycloaddition of dichloroketene to N,N-disubstituted 6-aminomethylene-b,7,8,9-tetra-hydro-5H-benzocyclohepten-5-ones afforded N,N-disubstituted 4-amino-3,3-dichloro-3,4,6,7-tetrahydro-5H-benzo[3,4]cyclohepta[2,l-b]pyran-2-ones only in the case of aromatic or strong hindering aliphatic N-substitution. The adducts gave N,N-disubstituted 4-amino-3-chloro-b,7-dihydro-5H-benzo[3,4]cyclohepta[2,l-b]pyran-2-ones by dehydrochlorination with collidine. Upon chromatography on neutral alumina, two products were instead isolated in the case of usual aliphatic N-substitution (diethylamine, piperidine), namely 6-(2,2-dichloroethylidene)-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one and the dehydrochlorinated 2-pyrone; this latter was the sole product in the case of pyrrolidine substitution. The 1,4-cycloaddition of sulfene occurred readily to give N,N-disubstituted 4-amino-3,4,6,7-tetrahydro-5H-benzo[3,4]cyclohepta-[1,2-e]-1,2-oxathiin 2,2-dioxidesin the case of both aliphatic and partially aromatic N-substitution. 相似文献
17.
The chlorination of N-acyl derivatives of p-aminophenols can provide either N-acyl-2,3,6-trichloro-4-aminophenols or N-acyl-2,3,5,6-tetrachloro-1,4-benzoquinone imines depending on solvent nature, process temperature, and molar ratio initial compound-chlorine. The chlorination of N-acyl-4-amino-1-naphthols affords only N-acyl-2,3-dichloro-1,4-naphthoquinone imines. N,N'-Diacyl-1,4-phenylenediamines give rise on chlorination to a mixture of 2,5-dichloro-, 2,6-dichloro-, and 2,3-dichloro-N,N'-diacyl-1,4-phenylenediamines. 相似文献
18.
Ganushchak N. I. Romanyuk A. L. Litvin B. L. Lys R. I. Polishchuk O. P. 《Russian Journal of General Chemistry》2001,71(2):286-289
2,3-Bis(benzotriazol-1-yl)-1,4-naphthoquinone reacts with aliphatic and aromatic amines to give the corresponding 2-amino-3-(benzotriazol-1yl)-1,4-naphthoquinones, and its reaction with alkali gives 2-hydroxy-3-(benzotriazol-1-yl)-1,4-naphthoquinone. 相似文献
19.
V. Yu. Korotaev Yu. A. Skorik A. Yu. Barkov M. I. Kodess A. Ya. Zapevalov 《Russian Chemical Bulletin》2005,54(11):2545-2549
3,3,3-Trifluoro-N′-(3-trifluoromethylphenyl)-1,2-propanediamine (5) was synthesized by the reaction of 2-diazo-1,1,1-trifluoro-3-nitropropane or 3,3,3-trifluoro-1-nitropropene with 3-aminobenzotrifluoride
followed by the reduction of the nitro group. The Michael 1,4-addition of diamine 5 to acrylic acid occurs only at the N(1) atom and affords N-mono-or N,N-dicarboxyethyl derivatives 6 and 7, depending on the reactant ratio. Protolytic equilibria 5–7 in aqueous solutions were studied by pH-potentiometry and UV spectroscopy. Only the aliphatic amino group can be protonated
in an aqueous solution, while the aromatic amino group remains unprotonated even in 12 M HCl. The stability constants of transition metal (Cu2+, Ni2+, Zn2+) complexes with ligands 5–7 were determined by pH-potentiometric titration. The stability of the complexes and selectivity of the ligands toward Cu2+ ions increase with an increase in the number of N-carboxyethyl groups.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2465–2469, November, 2005. 相似文献
20.
The geometric parameters, the charge distribution, and the energetics of N-methyl-2-(N-ethylanilino)-3-(indol-1-yl)-and N-methyl-2-(N-ethylanilino)-3-(indol-3-yl)maleimides and their conjugated acids were studied by density functional theory calculations
at the B3LYP/6-31G(d) level. The mechanism of the tandem hydride transfer/cyclization sequence, which occurs after protonation
of N-methyl-2-(N-ethylanilino)-3-(indol-1-yl)-and N-methyl-2-(N-ethylanilino)-3-(indol-3-yl)maleimides, was analyzed. The investigation of the potential energy surface for the tandem hydride
transfer/cyclization of the iminium cation that formed upon protonation revealed that the hydride transfer followed by intramolecular
cyclization at position 7 of the indole fragment in N-methyl-2-(N-ethylanilino)-3-(indol-1-yl)maleimide is the preferable process, unlike alternative intramolecular cyclization involving
the cationic center at the C(2) atom of the indole fragment and the benzene ring of the N-ethylaniline fragment of the indoleninium cation in N-methyl-2-(N-ethylanilino)-3-(indol-3-yl)maleimide. A study of the key intermediates of the assumed reaction mechanism demonstrated that
these intermediates are actually stationary points on the potential energy surface (minima and transition states).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2069–2073, December, 2006. 相似文献