Synthesis of Boron-containing Complexes of 1-(2-hydroxyphenyl)-3-phenyl-2-propen-1-one

Condensation of o-hydroxyacetophenone with benzaldehyde in alcohol in the presence of a triple excess of a sodium hydroxide solution leads to 2'-hydroxychalcone sodium salt. The latter was heated with boron trifluoride etherate in toluene to a 2'-hydroxychalcone boron fluoride complex in which the boron atom is coordinated to the carbonyl oxygen atom. The same complex was obtained by boiling of the o-hydroxyacetophenone boron fluoride complex with benzaldehyde in acetic anhydride.     

Synthesis and separation of diastereoisomeric 1-aryl-3-piperidino(morpholino)-2-phenylpropan-1-ols and their hydrochlorides

1-Aryl-3-piperidino(morpholino)-2-phenylpropan-1-ols were synthesized by reduction of the corresponding 1-aryl-3-piperidino(morpholino)-2-phenylpropan-1-ones with lithium tetrahydridoaluminate, and the products were separated into erythro and threo isomers by fractional crystallization. Their relative configuration and diastereoisomeric purity was determined by ¹H NMR spectroscopy.     

Synthesis and photolysis of copolymers with 1-(4-carbethoxyphenyl)-2-propen-1-one structural units

New light-sensitive copolymers containing 1-(4-carbethoxyphenyl)-2-propen-1-one (PCOOEt) chromophore and as comonomer styrene (S), vinyl acetate (VAC), ethyl acrylate (EA), phenyl acrylate (PhA), acrylonitrile (AN) and 1-buten-3-one (MVK) were prepared. Copolymers with MVK were crosslinked. In the copolymerization with VAC, an oligomer with M_GPC about 5000 Dalton and rich in PCOOEt is formed initially. Later, after consumption of PCOOEt, VAC polymerizes to high molecular weight. The oligomers are built in the main chain of VAC. Since the ketone-containing structures are only in the oligomeric part and in the side-chains, no decrease of the molecular weight, as followed by viscometry, was observed during photolysis. Copolymers of PCOOEt with EA, PhA, S and AN degrade under 366 nm irradiation in benzene or dimethylformamide solution with a quantum yield of main chain scission of the same order of magnitude as homopolymer. The quenching of the photolysis of copolymers shows that the reactivity of the triplet state is influenced by the comonomer. A comparison of quenching constants for copolymers with those of homopolymers indicate that self-quenching is not an important deactivation route of the triplet carbonyl group.     

Synthesis and spectroscopic studies of some heterocyclic compounds. Reaction of 3-aryl-1-phenyl-2-propen-1-ones with ethyl phenylacetate

3-Aryl-1-phenyl-2-propen-1-one I reacted with ethyl phenylacetate (II) in the presence sodium ethoxide at room temperature to give the corresponding ethyl β-aryl-γ-benzoyl-α-phenyl-butyrate III. However,' when the same ketones were refluxed with ethyl phenylacetate, they gave the corresponding 4-aryI-3,6-diphenyl-3,4-dihydro-2H-pyran-2-ones IV. The reactions of III and IV with hydrazine hydrate afforded the corresponding hydrazones VI and 2-pyridones VIII, respectively. The structure and configuration of the products are based on chemical and spectroscopic evidence.     

环状碳酸酯5,5-二甲基-1,3-二噁烷-2-酮的合成

在三乙胺存在下,2,2-二甲基-1,3-丙二醇和氯甲酸乙酯反应合成了环状碳酸酯5,5-二甲基-1,3-二噁烷-2-酮,其结构经1H NMR和IR表征。提出了可能的反应机理。     

Synthesis and stereochemistry of 2, 2-dimethyl-5-aryl-4-benzoyl-1,3-dioxolanes

The reaction of 3-aryl-2-benzoyloxiranes with acetone in the presence of catalytic amounts of boron trifluoride etherate leads to the formation of mixtures of cis and trans isomers (3070) of 2,2-dimethyl-5-aryl-4-benzoyl-1,3-dioxolanes, the structures and stereochemistry of which were established on the basis of data from their PMR spectra, measurement of the Overhauser nuclear effect, and some chemical transformations.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 888–891, July, 1979.     

Concise synthesis of dihydrochalcones via palladium-catalyzed coupling of aryl halides and 1-aryl-2-propen-1-ols

An expedient route to substituted dihydrochalcones is reported. The key step is a palladium-assisted arylation of 1-aryl-2-propen-1-ols. This two-step/one-purification process allows the synthesis of a wide range of compounds with original substitution patterns, including polyphenolic derivatives.     

Synthesis of 1-aryl-2-propanones

A new convenient synthesis of a series of 1-aryl-2-propanones using aromatic amines as precursors, via diazo-reaction and improved Meerwein arylation reaction under mild conditions, was achieved. In addition, 1-[3,5-bis(trifluoromethyl)phenyl]-2-propanone is a new compound among the synthesized compounds. This approach is an efficient synthetic method for the aryl-propanones with different substituting groups. __________ Translated from Chinese Journal of Organic Chemistry, 2007, 27(10): 1244–1249 [译自: 有机化学]     

Synthesis and structure of 2-aryl-2,4-dimethyl-1,2,3,4-tetrahydroquinolines and 1,3-disubstituted indenes

It has been shown that the intramolecular cyclization of N-(1-arylbutenyl)arylamines under acid catalysis conditions may proceed in two directions with the formation of 2-aryl-2,4-dimethyl-1,2,3,4-tetrahydroquinolines and 1,3 disubstituted indenes.     

Synthesis of 1-aryl-2-alkenyldiazene 1-oxides

1-Aryl-2-alkenyldiazene 1-oxides were prepared by the reactions of 1-aryl-2-bromodiazene 1-oxides with olefins followed by dehydrobromination of the intermediate 1-aryl-2-(-bromoalkyl)diazene 1-oxides by triethylamine.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 924–927, May, 1995.This work was carried out at the Scientific Educational Center of the Institute of Organic Chemistry of the RAS with financial support of the Russian Foundation for Basic Research (Project No. 93-03-18461).     

Synthesis of 2, 2 -dimethyl-1-p-tolyl-1-hydroxypropane and 2,2-dimethyl-1-p-tolyl-1-oxopropane

Conclusions 2,2-Dimethyl-1-p-tolyl-1-hydroxypropane and 2,2-dimethyl-1-p-tolyl-1-oxopropane were obtained for the first time.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 149–150, January, 1973.     

Heterocyclic compounds from 3,3-dimercapto-1 -aryl-2-propen-1-ones. Note 2. Condensation with o-aminothophenol and o-aminophenol

The condensation of 3,3-dimercapto-1-phenyl-2-propen-1-one with o-aminothiophenol and o-aminophenol in hot xylene gave 2-phenacylbenzothiazole ( 3 ) and 2-phenacylbenzoxazole ( 5 ). When the reaction with o-aminophenol was carried out in hot benzene, 2-beuzoylthioacctamidophenol ( 4 ) was obtained, which, heated in hot xylene gave 5. Ethyl benzoylacetale by reaction with o-aminothiophenol gave 3 , whereas by reaction with o-aminophenol gave no heterocyclic compound. However, we were able to isolate 2-benzoylacetamidophenol ( 6 ), ethyl β-phenyl-β-(o-hydroxy)phenyliminopropionate ( 7 ), and 2-[β-(o-hydroxy)anilino] cinnamoylamidophenol ( 8 ). Ir and nmr spectra of synthesized compounds point out the existence of tautomers.     

Synthesis of Alkyl 4-(1-Alkyl-2-aryl-2-oxoethyl)-5,5-dimethyl-2-oxotetrahydrofuran-3-carboxylates

Zinc enolates derived from 1-aryl-2-bromoalkanones react with alkyl 5,5-dimethyl-2-oxo-2,5-dihydrofuran-3-carboxylates to give alkyl 4-(1-alkyl-2-aryl-2-oxoethyl)-5,5-dimethyl-2-oxotetrahydrofuran-3-carboxylates. Reactions of the latter with amines, such as p-toluidine, cyclohexylamine, and piperidine, lead to the corresponding carboxamides.     

1—十二烷基氮杂环庚烷—2—酮的合成

已内酰胺与溴代十二烷在氢氧化钾的作用下，于甲苯中进行Ｎ－烷基化反应，合成了１－＋二烷基氮杂环庚烷－２－酮，收率８８％－９２％。     

1－十二烷基氮杂环庚烷－2－酮的合成

己内酰胺与溴代十二烷在氢氧化钾的作用下，于甲苯中进行Ｎ－烷基化反应，合成了１－十二烷基氮杂环庚烷－２－酮，收率８８％～９２％。