Synthesis of 4-substituted 1,5-diaryl-3-diphenylmethoxy-3-pyrrolin-2-ones and their [1,5]-sigmatropic rearrangement

Reactions of 1,4,5-trisubstituted 3-hydroxy-3-pyrrolin-2-ones with diphenyldiazomethane yield the O-alkylation products. Thermolysis of 1,5-diaryl-4-heteroyl-3-hydroxy-3-pyrrolin-2-ones is accompanied with suprafacial [1,5]-sigmatropic rearrangement.     

Synthesis of spirobiindanes via bis-cyclization reaction of the 1,5-diaryl-3-pentanones catalyzed by heteropoly acids

Bis-cyclization reaction of the 1,5-diaryl-3-pentanones catalyzed by heteropoly acids (HPAs) was examined for the first time, and a series of spirobiindanes were synthesized. 1,5-Diaryl-3-pentanones were refluxed and dehydrated in toluene in the presence of 0.15 equiv of a heteropoly acid to furnish spirobiindanes in moderate to high yield. For the known 4,4′-dibromo-7,7′-dimethoxy-1,1′-spirobiindane, the yield was upgraded from 66% to 80%.     

Synthesis and Biological Activity of 4-Hydroxy-3-(1,5-diaryl-3-oxo-pent-4-enyl)chromen-2-ones

The substituted warfarin acid chalcones have been prepared by condensation of warfarin acid and aromatic/aliphatic aldehyde using aq. NaOH as catalyst. The method is simple, cost‐effective and gives good yield in a short reaction time. All the compounds synthesized have been characterized by IR, NMR and Mass spectra. A new series of 4‐hydroxy‐3‐(3‐oxo‐1,5‐diaryl‐3‐oxo‐pent‐4‐enyl)‐chromen‐2‐ones were synthesized and submitted to biological activity. Result of the biological screening showed the compounds 3b , 3h being the most effective among the various treatments in antimicrobial screening. Compounds 3c , 3d , 3k and 3l showed moderate activity against the microorganisms tested. Compounds 3e , 3h have shown good antifungal activity.     

3-丙酰基-2,5-二芳基-1,3,4-噁唑啉类化合物的合成

3-丙酰基-2;5-二芳基-1;3;4-噁唑啉类化合物的合成;噁唑啉;衍生物;合成;结构表征     

Synthesis of methyl 1,5-diaryl-1H-pyrrole-2-carboxylates via acid-catalyzed ring-opening/ring-closure sequence

A facile synthesis of methyl 1,5-diaryl-1H-pyrrole-2-carboxylates was reported in this article. Acid-catalyzed reaction of methyl 2-aroyl-1-phenoxycyclopropanecarboxylates with aromatic amines underwent smoothly to give methyl 1,5-diaryl-1H-pyrrole-2-carboxylates in high to excellent yields under mild conditions.     

Reactions of 1,5-diaryl-4-heteroyl-3-hydroxy-3-pyrrolin-2-ones with arylamines and butylamine

1,5-Diaryl-4-[2-thienoyl(furanoyl)]-3-hydroxy-3-pyrrolin-2-ones reacted with aromatic amines to form arylamino-3-pyrrolin-2-ones. Reactions with butylamine occurred via intermediate salt formation followed by their transformation into 3-butylamino-3-pyrrolin-2-ones at heating.     

Recyclization of 2-alkoxycarbonylmethyl-1,5-diaryl-2-hydroxy-2,3-dihydropyrrol-3-ones by hydrazine

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, p. 1698, December, 1988.     

Synthesis and tautomerism of 5,7-diaryl-4,7(6,7)-dihydrotetrazolo[1,5a]pyrimidines

5,7-Diaryl-4,7(6,7)-dihydrotetrazolo[1,5-a]pyrimidines were synthesized by the cyclocondensation of 5-aminotetrazole with chalcones. The tautomerism of the compounds obtained is discussed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1489–1493, November, 1988.     

Synthesis and tautomerism of 5,7-diaryl-3-cyano-and 5,7-diaryl-3-ethoxycarbonyl-4,7(6,7)-dihydropyrazolo[1,5-<Emphasis Type="Italic">a</Emphasis>]pyrimidines

The cyclocondensation of 3-amino-4-cyanopyrazole and 3-amino-4-ethoxycarbonylpyrazole with 1,3-diaryl-2,3-propen-1-ones gives the corresponding 3-substituted 5,7-diaryl-4,7(6,7)-dihydropyrazolo[1,5-a]pyrimidines. Their tautomeric composition in solution has been investigated by ¹H NMR. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1824–1832, December, 2007.     

Five-membered 2,3-dioxoheterocycles 15. Synthesis and [1,3]-sigmatropic rearrangement of 1,5-diaryl-3-diphenylmethoxy-4-ethoxycarbonyl-2,5-dihydropyrrol-2-ones

Ethyl oxaloacetate reacts with a mixture of an aromatic aldehyde and an arylamine to give 1,5-diaryl-4-ethoxycarbonyltetrahydropyrrole-2,3-diones, which react with diphenyldiazomethane to give the O-alkylation products. On heating, the latter undergo suprafacial [1,3]-sigmatropic rearrangement to 1,5-diaryl-4-diphenylmethyl-4-ethoxycarbonyltetrahydropyrrole-2,3-diones. The effects of the type of migrating group on the rearrangement are discussed.For Communication 14, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 753–757, June, 1990.     

A general route to 3-unsubstituted 1,5-diaryl-2,4-pentanediones and -4-Methoxy-2-pentanones

2-Isoxazolines are converted to corresponding 3-hydroxyketones which are used as precursors to produce new 3-unsubstituted 1,5-diaryl-2,4-pentanediones and -4-methoxy-2-pentanones.     

Synthesis of 1,2-diaryl-2-imidazolines

Polyphosphoric acid and N-aryl-N′-benzoylethylenediamines in a type of Bischler-Napieralski reaction afforded 1,2-diaryl-2-imidazolines in good yields, rather than the 2,3-dihydro-1H-[1,4]-benzodiazepines. Blocking of the amino nitrogen by a methyl or ethyl group, to avoid imidazoline formation, gave starting material rather than the expected dihydrobenzodiazepine. When p-tosyl was the blocking group, imidazoline was again the only product isolated. Analytical and spectroscopic data of several unreported 1,2-diaryl-2-imidazolines are presented.     

Synthesis of 1,4-diaryl-2,5-dioxopiperazines

A new method for the synthesis of 1,4-dlaryl-2,5-dioxopiperazines by the condensation of chloroacetanilides in the presence of sodium in anhydrous solvents, has been developed. The evolution of hydrogen shows the nucleophilic nature of the condensation.     

Synthesis of novel 3-substituted 1,5-benzodiazepine derivatives

This paper describes an improved method for the synthesis of 3-(3-chloroquinoxalin-2-yl)-1,2-dihydro-1-formyl-2-oxo-3H-1,5-benzodiazepine (2) and its conversions into novel 3-substituted 1,5-benzodiazepine derivatives (3a,b and 4a,b).     

Synthesis of perhydro-1,5-dioxa-3-azepine derivatives

N-Acyl-, N-alkoxycarbonyl-, and N-benzenesulfonylperhydro-1,5-dioxa-3-azepine derivatives were obtained in 9–20% yields by condensation of ethylene glycol with unsubstituted amides, urethanes, and formaldehyde in refluxing xylene in the presence of a catalyst (concentrated HCl).Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 25–26, January, 1971.     

Synthesis and chemistry of 3-tert-butyl-1,5-diaminopyrazole

N-Amination of 3-amino-5-tert-butylpyrazole 11 with hydroxylamine-O-sulfonic acid gave the 1,5-diaminopyrazole 12 with good regiochemical control. The reactions of 12 with certain electrophiles (e.g. acetic anhydride, DMF acetal, aromatic aldehydes, methoxymethylene Meldrum's acid) took place at one (or both) of the amino groups and no cyclised products were obtained. Reaction of 12 with carbon disulfide followed by alkylation under basic conditions provided the pyrazolo[1,5-b]1,2,4-triazole 26 which is a useful photographic magenta coupler. Reactions of 12 with 1,2- and 1,3-dicarbonyl compounds (diketones and ketoesters) provided new pyrazolo[1,5-b]1,2,4-triazines 29, 30, 42 and 43 and the first derivatives of the pyrazolo[1,5-b]1,2,4-triazepine system 31 and 35-36. The X-ray crystal structure of the pyrazolotriazepine 33 is reported.     

Synthesis of 1,3-diaryl-4,7-phenanthrolines

A number of new 1,3-diaryl-4,7-phenanthrolines were synthesized by heterocyclization of arylidene-6-quinolylamines with acetophenones in the presence of an acidic catalyst. Intermediate amino ketones and side products, viz., N-(R¹-benzyl)-6-quinolylamines and ,-unsaturated ketones, were isolated. The IR, UV, PMR, and mass spectra of the synthesized compounds are discussed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1398–1401, October, 1985.     

Synthesis of 1,3-diaryl-2,2-dichloroethyleneimines

1,3-Diaryl-2-dichloroethyleneimines were synthesized by the reaction of aromatic Schiff bases with chloroform in the presence of potassium tert-butoxide. Several properties of these compounds were studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 180–181, February, 1972.