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1.
Treatment of γ-bromodypnone with arylhydrazines gives differently structured products, i.e. γ-bromo-dypnone hydrazones, 1-aryl-3,5-diphenyl-1,4-dihydropyridazines,
1-aryl-3,5-diphenyl-1,6-dihydro-pyridazines, and aromatic 1,3,5-triarylpyridazinium salts. We have studied the pattern of
formation of all of the products and their properties. Heating an alcohol solution of 1,3,5-triphenyl-1,4-dihydro-pyridazine
gives N,2,4-triphenyl-1H-pyrrole-1-amine or to a 1,3,5-triphenylpyridazinium salt dependent upon the acidity of the medium.
The product of addition of HBr to the 1,6-dihydropyridazine system is 5-bromo-1-(4-nitrophenyl)-3,5-diphenyl-1,4,5,6-tetrahydropyridazine. 相似文献
2.
The reaction of 4-bromo-1,3-diphenyl-2-buten-1-one with thiourea or N,N′-diphenylthiourea gives 2-(2-amino-4-phenyl-4,5-dihydro-1,3-thiazol-4-yl)-and
2-[3,4-diphenyl-2-(phenylimino)-1,3-thiazolidin-4-yl]-1-phenyl-1-ethanone — the products of nucleophilic substitution of the
halogen atom and Michael addition at position 3 of the 2-buten-1-one system. A similar reaction with thiosemicarbazide and
1-phenylthiosemicarbazide gives the 4-(2-oxo-2-phenylethyl)-4-phenyl-and 4-(2-oxo-2-phenylethyl)-3,4-diphenyl-1,3-thiazolidin-2-one
hydrobromides respectively.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 103–110, January, 2008. 相似文献
3.
The condensation of 1,3-diaryl-4-bromo-2-buten-1-ones with o-phenylenediamine leads to 2-[2,4-diaryl-1H-pyrrol-1-yl]phenylamines.
Heating solutions of these compounds in formic acid leads to formylation and intramolecular condensation to give 1,3-diarylpyrrolo[1,2-a]quinoxalines. The acylation of 2-[2,4-diphenyl-1H-pyrrol-1-yl]phenylamine with acetic anhydride in acetic acid leads to an
acetamide, which readily cyclizes to give 4-methyl-1,3-diphenylpyrrolo[1,2-a]quinoxaline upon heating with POCl3. 相似文献
4.
A series of 1-aryl-2,4-diphenylpyrroles were obtained by the reaction of 4-bromo-1,3-diphenyl-2-buten-1-one (γ-bromodypnone)
with substituted anilines in the presence of sodium acetate. In the reaction with di-and trimethylenediamines the corresponding
1,2-and 1,3-di(N-pyrryl)alkanes were obtained.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 848–853, June, 2006. 相似文献
5.
L. M. Potikha A. R. Turelyk V. A. Kovtunenko A. V. Turov G. V. Palamarchuk R. I. Zubatyuk O. V. Shishkin 《Chemistry of Heterocyclic Compounds》2010,46(6):742-753
(Z)-4-Bromo-1,3-di(2-thienyl)-2-buten-1-one was obtained by the bromination of 1,3-di(2-thienyl)-2-buten-1-one by NBS in anhydrous
CCl4. The starting butanone was obtained by the condensation of 1-(2-thienyl)-1-ethanone by the action of SOCl2. The reaction of (Z)-4-bromo-1,3-di(2-thienyl)-2-buten-1-one with tertiary amines such as Et3N, pyridine, 1-alkyl-1,3-diazole, 1-alkylbenzimidazole, and 1-alkyl-1,2,4-triazole leads to quaternary salts. The azolium
salts cyclize by the action of base to give di(2-thienyl)azolo[a]pyridinium derivatives. 3-Methyl-6,8-di(2-thienyl)[1,3]thiazolo[3,2-a]pyridin-4-ium
and 2,4-di(2-thienyl)pyrido[2,1-b]benzothiazol-10-ium bromides were obtained by the same procedure but without separating
the intermediate quaternary salts. 相似文献
6.
Alemayehu Mekonnen Andreas Westerlund Martina Havelkova Alexandre Descomps 《合成通讯》2013,43(14):2472-2480
Synthetic procedures for the preparation of 1-bromo-3-butyn-2-one and 1,3-dibromo-3-buten-2-one are given. These compounds are prepared from 2-bromomethyl-2-vinyl-1,3-dioxolane, which can readily be prepared from 2-ethyl- 2-methyl-1,3-dioxolane. The synthetic routes are as follows: 2-bromomethyl-2-vinyl-1,3-dioxolane is converted to 2-(1,2-dibromoethyl)-2-bromomethyl-1,3-dioxolane. Double dehydrobromination with tBuOK affords 2-ethynyl-2-bromomethyl-1,3-dioxolane. Formolysis with formic acid gives 1-bromo-3-butyn-2-one. Deacetalized 2-bromoethyl-2-vinyl-1,3-dioxolane was treated with Br2 and Li2CO3/12-crown-4 in tetrahydrofuran to give 1,3-dibrom-3-buten-2-one in moderate yield. 相似文献
7.
L. M. Potikha A. R. Turelyk V. A. Kovtunenko 《Chemistry of Heterocyclic Compounds》2011,47(6):745-754
Fusion of 4-bromo-1,3-diphenyl-2-buten-1-ones (γ-bromodypnones) with 1,2-dimethyl-1H-benzimidazole and further treatment of
the reaction product with a base (morpholine) gives 7,9-diaryl-5-methyl5,10-dihydroazepino[1,2-a]benzimidazol-11-ium bromides. The reaction of γ-bromodypnone with 1-alkyl-2-methyl-1H-imidazoles in benzene at 25 °C gives
quaternary azolium salts. Upon heating their solutions in alcohol in the presence of K2CO3 the latter cyclize to 1-R-6,8-diaryl-1,5-dihydroimidazo[1,2-a]azepin-4-ium bromides or 1-R-6,8-diaryl-1H-imidazo[1,2-a]azepines
depending on the nature of the substituent in the benzene rings and the substituent at the N(1) atom of the imidazole. 相似文献
8.
The nitrosation of the oximes of 4-phenyl-3-buten-2-one and 1,3-diphenyl-2-propen-1-one under oxygen has been reinvestigated. In addition to 4-oxo- and 4-oximino-4H-pyrazole 1,2-dioxides previously reported, the reactions give 4-nitro-1-hydroxypyrazole 2-oxides. In the case of 1,3-diphenyl-2-propen-1-one oxime the nitrosation reaction also gives 3,5-diphenyl-4-nitrato-4,5-dihydroisoxazole. Evidence is presented suggesting that the nitrate ester is formed through the rearrangement of a peroxynitrite intermediate. 相似文献
9.
John F. Hansen John A. Easter David A. Eckert Karen J. Hunt David A. Little 《Journal of heterocyclic chemistry》1994,31(2):281-286
Nitrosation of the oximes of 3-bromo-3-penten-2-one, 3-bromo-4-phenyl-3-buten-2-one, and 2-bromo-1,3-diphenyl-2-propen-1-one using sodium nitrite in acetic acid gave low yields of 4-pyrazolone 1,2-dioxides. Nitrosation using butyl nitrite in the presence of copper(II) sulfate and pyridine in aqueous ethanol produced insoluble copper complexes from which 3,5-dimethyl-, 3-methyl-5-phenyl-, and 3,5-diphenyl-4-bromo-1-hydroxypyrazole 2-oxides could be liberated by treatment with dilute potassium hydroxide, filtration, and acidification of the filtrate. High yields were obtained with the first two oximes, but, presumably due to unfavorable stereochemistry of the oxime, the diphenyl derivative gave a lower yield of the complex, accompanied by 4-bromo- and 4-nitro-3,5-diphenylisoxazole and 4-oximino-3,5-diphenyl-4,5-dihydroisoxazole. 相似文献
10.
L. M. Potikha A. R. Turelik V. A. Kovtunenko 《Chemistry of Heterocyclic Compounds》2009,45(10):1184-1189
Bromination of 1,3-bis(aryl)-2-buten-1-ones by N-bromosuccinimide in anhydrous carbon tetrachloride gives Z-1,3-bis(aryl)-4-bromo-2-buten-1-ones.
The effect of the nature of substituent in the benzene ring on the course of a reaction with nucleophiles has been studied.
Heating an alcohol solution of these ketones (Ar = 4-MeOC6H4, 4-ClC6H4) in the presence of acid or in the presence of base (Ar = Ph) gave 2,4-bis(aryl)furans. Treatment of 1,3-bis(aryl)-4-bromo-2-buten-1-ones
with thioacetamide gave 2,4-bis(aryl)thiophenes. The oxidation of the halo-substituted dypnones with H2O2/NaOH gave (3-bromomethyl-3-aryl-2-oxiranyl)(aryl)methanones. The reaction of halo-substituted dypnones with aryl hydrazines
gave 1,3,5-triaryl-1,6-dihydropyridazines or 1,3,5-triarylpyridazinium bromides depending on the structure of the reagents. 相似文献
11.
G. A. Gazieva P. V. Lozhkin A. N. Kravchenko 《Chemistry of Heterocyclic Compounds》2007,43(11):1406-1410
The α-ureidoalkylation of imidazolidine-2,4-dione, urea, carboxylic acid amides, and sulfonamides has been studied using 1,3-bis(hydroxymethyl)-imidazolidin-2-one
as ureidoalkylating agent. Methods have been developed for the synthesis of 1,3-bis(2,4-dioxoimidazolidin-1-ylmethyl)-, 1,3-bis(acetylaminomethyl)-,
1,3-bis(benzoylaminomethyl)-, 1,3-bis(phenylsulfonylaminomethyl)-, and 1,3-bis(p-toluenesulfonylaminomethyl)imidazolidin-2-ones.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1655–1659, November, 2007. 相似文献
12.
Ioannou TA Koutentis PA Krassos H Loizou G Re DL 《Organic & biomolecular chemistry》2012,10(7):1339-1348
Regioselective nucleophilic addition of bisnucleophiles 1,2-benzenediamine, 2-amino-benzenethiol, and N-phenyl-1,2-benzenediamine to 1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-one (1) at C6 followed by intramolecular cyclocondensation at the C7 carbonyl afforded highly coloured tetracenes 1,3-diphenyl-1,6-dihydro-[1,2,4]triazino[5,6-b]phenazin-4-ium 4-methylbenzenesulfonate (12), 1,3-diphenyl-1H-[1,2,4]triazino[6,5-b]phenothiazine (14) and 1,3,11-triphenyl-1,6-dihydro-[1,2,4]triazino[5,6-b]phenazin-11-ium 4-methylbenzenesulfonate (15), respectively. Neutralization of the latter with alkali gave the free base 1,3,11-triphenyl-1H-[1,2,4]triazino[5,6-b]phenazin-11-ium-6-ide (16). Furthermore, the benzotriazinone 1 reacts with dimethyl malonate to give 6-(methoxycarbonyl)-7-oxo-1,3-diphenyl-7H-benzofuro[5,6-e][1,2,4]triazin-1-ium-4-ide (17) in 74% yield, while with S(4)N(4) [5,6-c]-thiadiazolo-7-oxo-1,3-diphenyl-1,2,4-benzotriazine (22) was formed in 15% yield. The free bases 16 and 17 display negative solvatochromism, which supports charge separated ground states similar to those of zwitterionic biscyanines, and DFT calculations at the UB3LYP/6-31G(d) level afford ΔE(ST) values of -13.6 and -18.7 kcal mol(-1), respectively that strongly favour the singlet ground state. All ring systems described are new and fully characterized. 相似文献
13.
Dr. J. Schantl 《Monatshefte für Chemie / Chemical Monthly》1974,105(2):322-326
1-Phenyl-1-phenylazoethylene (α-phenylazostyrene,2) cannot be isolated, as, functioning both as a heterodiene and a dienophile, it reacts to its (4+2)-cyclodimer, 1,3,6-triphenyl-6-phenylazo-1,4,5,6-tetrahydropyridazine (3). In the presence of the competing dienophile 3-buten-2-one (4) the intermediate2 is partially trapped to 6-acetyl-1,3-diphenyl-1,4,5,6-tetrahydropyridazine (5). 相似文献
14.
Rulev A. Yu. Fedorov S. V. Chuvashev Yu. A. Voronkov M. G. 《Russian Journal of Organic Chemistry》2003,39(5):646-649
Piperidine reacts with 3-bromo-3-buten-2-one to give a mixture of 3,4-dipiperidinobutan-2-one and 3-piperidino-3-buten-2-one. The latter is also formed by the action of a strong base (Et3N in THF or MeONa in MeOH) on the dipiperidino derivative. Analogous reaction of 2-bromo-3-phenylpropenal with N-methylaniline affords 2-[methyl(phenyl)amino]-3-phenylpropenal which is the first captodative formyl(amino)alkene having a weakly basic tertiary amino group. 相似文献
15.
R. S. Vartanyan A. L. Gyul'budagyan S. A. Vartanyan 《Chemistry of Heterocyclic Compounds》1984,20(4):370-372
The reaction of 5-amino-1,3-diphenylpyrazole with benzaldehyde gives 5-benzylideneamino-1,3-diphenylpyrazole, which then undergoes cyclization with mercaptoacetic acid to give 1,3,4-triphenyl-1H-pyrazolo[3,4-e][1,4]thiazepin-7-one.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 464–465, April, 1984. 相似文献
16.
L. M. Potikha A. R. Turelyk V. A. Kovtunenko A. V. Turov 《Chemistry of Heterocyclic Compounds》2010,46(1):82-95
The interaction of (Z)-1,3-diaryl-4-bromo-2-buten-1-ones with 1-substituted (benz)imidazoles in benzene gave (Z)-1-R-3-(2,4-diaryl-4-oxo-2-butenyl)-1H-imidazolium
bromides and (Z)-1-R-3-(2,4-diaryl-4-oxo-2-butenyl)-1H-benzimidazolium bromides which readily cyclize in the presence of base
to form derivatives of 7,9-diarylpyrido[1,2-a]benzimidazole and 6,8-diarylpyrimidazo[1,2-a]pyridine. The effects of the nature of substituents in the benzene ring of the diarylbutenones and the substituent at N(1)
in the (benz)imidazoles on the alkylation and cyclization reactions has been studied. The optimum conditions for the synthesis
of the 5-R-4-hydroxy-2,4-diphenyl-4,5-dihydro-1H-pyrido[1,2-a]benz-imidazol-10-ium, 5-R-2,4-diaryl-4-hydroxy-4,5-dihydro-3H-pyrido[1,2-a]benzimidazol-10-ium, and 5-R-2,4-diaryl-5H-pyrido[1,2-a]benzimidazol-10-ium
have been found. 相似文献
17.
O. V. Petrova M. V. Markova L. N. Sobenina L. V. Morozova A. I. Mikhaleva S. H. Hyun B. A. Trofimov 《Russian Chemical Bulletin》2009,58(1):115-118
Sterically hindered 2,5-diphenyl-and 2,3,5-triphenyl-1-vinylpyrroles have been obtained by the vinylation of the corresponding
NH-pyrroles with acetylene in superbasic catalytic system KOH—DMSO in up to 78% yield. 2,3,5-Triphenyl-1-vinylpyrrole has
also been obtained in 75% yield by the regioselective bromination of 2,3-diphenyl-1-vinylpyrrole with subsequent cross-coupling
of 5-bromo-2,3-diphenyl-1-vinylpyrrole with phenylmagnesium bromide in the presence of dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II).
2,5-Diphenyl- and 2,3,5-triphenyl-1-vinylpyrroles undergo a free-radical polymerization (AIBN, 80 °C) to form oligomers in
11 and 27% yield, respectively. 相似文献
18.
Alexandre Descomps 《合成通讯》2014,44(6):757-761
The unstable ketones 1-bromo-3-buten-2-one, 1-bromo-3-butyn-2-one, and 1,3-dibromo-3-buten-2-one can be obtained from the corresponding acetals in high yields by treating the acetals with anhydrous iron (III) chloride suspended on dry silica. A simplified procedure for preparing the reagent is also given. 相似文献
19.
2-Ethoxy-1,3-benzothiazin-4-one ( 6 ), 4,4-diphenyl-2-ethoxyoxazolin-5-one ( 10 ) and 1-benzyl-2-methoxyimidazolidine-4,5-dione ( 12 ) were prepared and were found to react with 1,1-bicyclo-hexenyl, 1,2,3,4-tetramethylbutadiene and 2,4-dimethyl-1,3-pentadiene to give Diels-Alder ad-ducts ( 8, 9, 13-18 ). 相似文献
20.
The reactions of 2-trichloromethylchromones with trimethylenediamine in ethanol at room temperature afford 2-(2-hydroxyaroylmethylene)hexahydropyrimidines.
Under analogous conditions, 2-methylchromone gives a mixture ofN,N′-trimethylenebis[3-amino-1-(2′-hydroxyphenyl)-2-buten-1-one] andN,N′-trimethylenebis(imine) of 2-hydroxyacetophenone.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2140–2143, November, 1999. 相似文献