1,3-Thiazolidine-2,4-dione 2 has been synthesized by the cyclisation reaction of thiourea and chloroacetic acid in the presence of ethanol. The reaction of compound 2 with substituted aromatic aldehyde afforded the corresponding derivatives of substituted 5-benzylidene-1,3-thiazolidinone-2,4-dione 3a–d, which upon reflux with ω-bromoalkoxyphthalimide gave 2-{[-5-(substituted benzylidine)-2,4-dioxo-1,3-thiazolidine-3-yl]alkoxy} -1H-isoindole-1,3(2H)-dione 4a–i. Further, compounds 4a–i were treated with phenyl hydrazine and 2,4 dinitro phenyl hydrazine in the DMF to yield the title compound 2-[5-oxo-2,3-substituted diphenyl-2H-pyrazolo[3,4-d][1,3]thiazol-6(5H)-yl)alkoxy]-1H-isoindole-1,3(2H)-dione 5a–r. Structures of newly synthesized compounds were established based on elemental analysis, IR, 1H NMR and mass spectral data. Synthesized compounds have been assayed for their antibacterial activities against B. subtilis, K. pneumoniae, P. aeruginosa and S. aureus and antifungal activities against A. fumigatus and C. albicans. 相似文献
A novel unsymmetrical and kink noncoplanar heterocyclic bisphenol-like monomer, 4-(4-hydroxynaphthalenyl)phthalazin-1-one
(2), was synthesized in a two-step reaction starting from 1-naphthol and
phthalic anhydride via Friedel-Crafts acylation reaction and cyclization with hydrazine hydrate. Two heterocyclic
poly(arylene ether)s were prepared conveniently from monomer 2 and two
activated dihalide monomers by a N-C coupling reaction. The polycondensation proceeded quantitatively in
N,N-dimethylacetamide in the presence of anhydrous potassium carbonate
and afford the polymers with inherent viscosities of 0.46 and 0.34 dL/g. Thermal analysis showed that the
polymers had excellent thermal properties. The glass transition temperatures were 277 °C and
316 °C respectively, and the temperatures of 5% weight loss were all above 500 °C in
nitrogen atmosphere. The unsymmetrical and kink noncoplanar structures of the polymers chains could disturb
interchain and intrachain interactions and make them amorphous and readily soluble in polar, aprotic solvents.
The dilute solution of the polymers in chloroform showed strong optical absorption in ultraviolet region,
and exhibited violet-blue fluorescence with emission maxima at 400-470 nm. 相似文献
A series of 3-(6-substituted phenyl-[1,2,4]-triazolo[3,4-b]-[1,3,4]-thiadiazol-3-yl)-1H-indoles (5a–l) were designed, synthesized and evaluated for anti-apoptotic Bcl-2-inhibitory activity. Synthesis of the target compounds was readily accomplished through a reaction of acyl hydrazide (1) with carbon disulfide in the presence of alcoholic potassium hydroxide to afford the corresponding intermediate potassium thiocarbamate salt (2), which underwent cyclization reaction in the presence of excess hydrazine hydrate to the corresponding triazole thiol (3). Further cyclisation reaction with substituted benzoyl chloride derivatives in the presence of phosphorous oxychloride afforded the final 6-phenyl-indol-3-yl [1,2,4]-triazolo[3,4-b]-[1,3,4]-thiadiazole compounds (5a–l). The novel series showed selective sub-micromolar IC50 growth-inhibitory activity against Bcl-2-expressing human cancer cell lines. The most potent 6-(2,4-dimethoxyphenyl) substituted analogue (5k) showed selective IC50 values of 0.31–0.7 µM against Bcl-2-expressing cell lines without inhibiting the Bcl-2-negative cell line (Jurkat). ELISA binding affinity assay (interruption of Bcl-2-Bim interaction) showed potent binding affinity for (5k) with an IC50 value of 0.32 µM. Moreover, it fulfils drug likeness criteria as a promising drug candidate. 相似文献
A novel rhodium(III)‐catalyzed direct functionalization of ortho C H bonds of benzoic acid derivatives and an intramolecular cyclization sequence generates 3‐substituted phthalides in moderate to good yields. This cascade cyclization involves a Grignard‐type arylation of an aldehyde and subsequent intramolecular nucleophilic substitution. No theoretical waste except for water is generated in the reaction. 相似文献
ABSTRACTA novel, simple and efficient synthetic protocol has been developed for the synthesis of a series of thiazolidine-4-one and 3H-thiazole derivatives via a one-pot four-component condensation-cyclization reaction of hydrazine with allyl isothiocyanate and an α-haloketone in the presence of various aldehydes. This new protocol produces novel thiazolidine-4-one and 3H-thiazole derivatives in excellent yields. The remarkable features of this methodology are high yields, easy work-up and a one-pot simple reaction method. 相似文献
The condensation of various thiosemicarbazones with methyl thiophene-2-carboximidate afforded the corresponding intermediates 2a–2h. Subsequent cyclization of the latter compounds with hexamethylphosphorous triamide constitutes a new route to the synthesis of novel highly functionalized thiadiazaphosphole derivatives 4a–4h. This method offers significant advantages such as efficiency, high yields and mild reaction conditions. 相似文献
A new [3+2] cycloaddition strategy for the direct synthesis of highly substituted pyrroles from the readily available α‐acylketene dithioacetals (or related substrates) and commercially available propargylamines under mild metal‐free conditions has been developed. In this reaction, the acyl group plays a critical role in driving the conjugate addition of propargylamine and further cyclization to give pyrroles. Furthermore, the wide scope was confirmed by the preparation of 1,2,3,4‐tetrasubstituted pyrroles (60–70% yields) via a formal 1,2‐acyl migrating [3+2] cycloaddition pathway with N‐methylprop‐2‐yn‐1‐amine as the secondary amine component. 相似文献
Synthesis of diindeno[1,2,3,4-defg: 1′,2′,3′,4′-mnop]chrysene (1), a portion of the C60 surface, was attempted through oxidative cyclization of tetrabenzo[5.5]fulvalene (2), dibenzo[gp]chrysene (3), and diphenylmethylidenefluorene (4) by SbF5/SO2CIF. Compounds 2 and 3 were oxidized to dications which then underwent a single cyclization to give precursors to 1. Compound 4 underwent two oxidative cyclizations to give a precursor to 1. AM1 calculations of the possible products from cyclization were consistent with preferential formation of the cyclized product with the lower ΔHf. Oxidative cyclization may offer a one-pot synthetic alternative for the preparation of unusual polycyclic aromatic hydrocarbons. 相似文献
The Pd‐catalyzed 5‐exo‐trig‐3‐exo‐trig cascade cyclization of 1,6‐enynes with a propargyl carbonate terminus offers the shortest synthetic route to variously substituted 2‐(bicyclo[3.1.0]hex‐1‐yl)acrylates, a novel class of prospective monomers for low‐shrinkage polymers. To apply this reaction to large‐scale preparations of the said bicyclic acrylates, a flexible Pd catalyst system with tunable reactivity has been developed. The dependence of the product and diastereomer distribution on both the reaction conditions, including the type of palladium catalyst used, and on the nature of the substrate has been investigated. A variety of methyl 2‐(bicyclo[3.1.0]hex‐1‐yl)acrylates and parent carboxylic acids as well as some of their derivatives of potential interest towards a technical application were prepared on a multigram scale. A general large‐scale synthesis of the cyclization precursors bearing one or two carbonyl groups in the tether is also disclosed. 相似文献
Abstract The heterofunctional condensation of cis-1,3.5,7-tetrahydroxy-1,3,5,7-tetraphenylcyclotetrasiloxane with dimethylchlorosilane has been studied. It was established that when the reaction proceeds under mild conditions tetraphenylcyclotetrasiloxane incompletely substituted with dimethylsiloxy groups is obtained, i.e., 1,3,5-tris(dimethylsiloxy)-7-hydroxy-1,3,5,7-tetraphenylcyclotetrasiloxane, while under certain conditions 1,3,5,7-tetrakis(dimethylsiloxy)-1,3,5,7-tetraphenylcyclotetrasiloxane is formed. The catalytic dehydrocondensation of 1,3,5-tris(dimethylsiloxy)-7-hydroxy-1,3,5,7-tetraphenylcyclotetrasiloxane both in a dilute and concentrated solutions in the presence of platinochlorohydric acid as a catalyst has been studied. It was shown that the reaction proceeds both by the mechanism of intramolecular cyclization with formation of a bicyclic compound and intermolecularly with formation of a tricyclic compound. The catalytic dehydrocondensation of 1,3,5,7-tetrakis-(hydriddimethylsiloxy)-1,3,5,7-tetraphenylcyclotetrasiloxane with cis-1,3,5,7-tetrahydroxy-1,3,5,7-tetraphenylcyclotetrasiloxane and with oligotetrols (m = 5, 10) was also studied. The reaction order, activation energies and dehydrocondensation rate constants were found. It was established that with an increase in the length (m) of the oligotetrols the degree of catalytic dehydrocondensation is reduced. It was shown that if the platinochlorohydric acid catalyst is replaced by anhydrous powdered caustic potassium a different configuration of the cyclotetrasiloxane skeleton is realized in polymers. 相似文献
Facile routes were achieved for the synthesis of novel fluorinated spiro[oxindole-thiazolidinone] fused with some sulfur and phosphorus heterocycles starting from 5-fluoro-3′-(4-fluorophenyl)-4′H-spiro[indole-3,2′-thiazolidine]-2,4′(1H)-dione (1) via its reaction with trifluoroacetamide, 2-chloro-6-fluorobenzaldehyde and hydrazine hydrate followed by treatment with some suitable sulfur and phosphorus reagents. The antioxidant activities of the synthesized compounds were also evaluated. 相似文献
ABSTRACT A novel three-component reaction between isocyanides, isothiocyanates, and oxiranes has been developed. An array of substituted oxathianes have been obtained in acceptable to good yields. The reaction product could be modulated using Bu3P or TBPAc as an organo-catalyst. This work offers an opportunity for the further implementation of isocyanides in library design. 相似文献
Both enantiomers of the novel amino alcohol (R)‐ and (S)‐ 2 are prepared from the corresponding enantiomer of the mandelic acid‐derived ethanediol 3 . The regioisomeric amino alcohols 1 and 2 are converted into the imines 7 and 8 , respectively. Titanium complexes 9 and 10 derived therefrom are used as catalysts for the addition of diethylzinc to benzaldehyde and yield the alcohol 11 in up to 92% ee. On the other hand, the chloro‐substituted titanium complexes 14 and 15 are able to mediate the Torgov cyclization reaction of the diketone 16 to give the estrone derivative 17 . In both reactions titanium complexes 10 and 15 derived of the novel amino alcohol 2 give higher enantioselectivities than the complexes 9 and 14 that are based on the regioisomeric amino alcohol 1 . 相似文献
Saccharin is hydrolyzed with two different acids to yield 1,2-di-acid. The di-acid, on chlorination with phosphorous pentachloride, gave 2-chlorosulfonylbenzoyl chloride. The 2-chlorosulfonylbenzoyl chloride on hydrazinolysis gave benzothiadiazinetrione, while with phenyl hydrazine it selectively yielded 2-phenylbenzothiadiazinetrione. 2-chlorosulfonoylbenzoyl chloride with different aromatic 1,2-diamines resulted in dibenzothiadiazocine derivatives. Electron-donating groups in the diamine facilitate while the electron-withdrawing groups retard the cyclization. However, aliphatic diamines, aniline and substituted anilines readily gave acyclic aminosulfonyl carboxybenzamides on condensation with 2-chlorosulfonylbenzoyl chloride. The di-acid and anhydride did not react with either hydrazine/phenyl hydrazine or amines to give the above products. However, when its ester derivative, isopropyl-2-chlorosulfonylbenzoate, condensed with hydrazine, it gave benzothiadiazinetrione. But the ester failed to react with phenyl hydrazine. All the condensation reactions were carried out at room temperature. 相似文献
A novel synthesis of quinolizidines by a cationic gold‐catalyzed double cyclization cascade has been developed. The reaction was initiated by the gold‐catalyzed 6‐exo‐dig cyclization of ynamides, which was followed by a second cyclization of an enamide intermediate to provide the corresponding quinolizidine derivatives. The utility of this reaction was demonstrated by application to the synthesis of multi‐substituted quinolizidines and by the total synthesis of a quinolizidine alkaloid, (±)‐lupinine.
The acylation of hydrazine hydrate with a series of saturated fatty acid chlorides containing from eight to 18 carbon atoms
was studied under a variety of conditions in order to obtain the desirable fatty acid monohydrazides. Optimum yields were
obtained (ranging from 31.5% to 75% as the series ascended from C-8 to C-18) for the even-numbered monohydrazide members through
the use of a large excess of hydrazine hydrate in several organic solvents. Diethyl ether was found to be suitable if the
acid chloride is dissolved in it and added slowly to a cold mixture of hydrazine hydrate in ether. The Schotten-Baumann technique
was found suitable for the preparation of the symmetrically substituted fatty acid dihydrazides in better than 82% yields
when one mole of hydrazine hydrate was acylated with two of acid chlorides. Physical and chemical properties of both series
of fatty nitrogen derivatives are briefly treated. Stearic monohydrazide was condensed with acetonylacetone to give a substituted
pyrrole. An unsymmetrical dihydrazide was prepared by the acylation of myristic monohydrazide with lauroyl chloride. Stearic
dimethylhydrazide was prepared by the acylation of dimethylhydrazine with stearoyl chloride. Two quaternizations of this product
were carried out.
Part I. JAOCS31, 151 ({dy1954}).
Presented at the AOCS Meeting, New York, October 1960. 相似文献
A new and facile synthetic route is proposed for the synthesis of some novel phenothiazines (5a–5g) based on the reaction of 2-amino substituted benzenethiols with p-tert-butyl phenol in good yield. The newly synthesized compounds were characterized by IR, 1H NMR and mass spectral studies. Their antimicrobial activities against three strains of bacteria: Bacillus subtilis, Bacillus megaterium, Escherichia coli, and two strains of fungi: Aspergillus niger and Aspergillus oryzae, were investigated. 相似文献