Synthesis of N-substituted pyrrole-3-carbaldehydes by hydroformamination of 2,5-dimethoxy-2,5-dihydrofuran

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, p. 1285, September, 1990.     

Catalytic hydroformamination of dihydrofurans

Conclusions A preparative method has been developed for the synthesis of 3-(N-alkyliminomethyl)-tetrahydrofurans and 3-(N, N-dialylaminomethyl)tetrahydrofurans by the hydroformamination of 2,3- and 2,5-dihydrofurans in the presence of HRh(CO)(PPh₃)₃.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1198–1199, May, 1989.     

Photochemical and chemical behaviour of 2,5-hydroperoxyhydroxy-2,5-dihydrofurans

From hydroxyhydroperoxides II and III a new bicyclic system, namely the 5,6-dioxabicyclo[2.1.1]hexane VII is obtained by photolysis or by protic acids. Epimer epoxides IV and XI are obtained on reaction with triethylamine.     

2,5-Dimethoxy-2,5-dihydrofurans in 1,3-dipolar cycloaddition reactions

Itis shown that 2,5-dimethoxy-2,5-dihydrofurans enter into 1,3-dipolar cycloaddition with benzonitrile N-oxides and with diphenylnitrilimines to form derivatives of 1,3-dimethoxy-6-phenyl-1,3,3a,6a-tetrahydrofuro[3,4-d]isoxazole and 1,3-dimethoxy-4,6-diphenyl-1,3,3a,-6a-tetrahydrofuro[3,4-d]pyrazole, respectively.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 150–151, February, 1971.     

Photochemical rearrangement of 5,5-diaryl-2,5-dihydrofurans

Direct irradiation of 5,5-diaryl-2,5-dihydrofurans results in a di-π-methane rearrangement to give 3-penten-1-one derivatives. Triplet sensitization leads to the formation of a 2-oxyabicyclo[2.1.0]pentane which is extremely sensitive to heat and oxygen.     

Liquid-phase hydroformylation of 2,3- and 2,5-dihydrofurans

The synthesis of 3-formyl derivatives of the tetrahydrofuran series was carried out by hydroformylation of 2,3-dihydrofuran and 2,5-dimethoxy-2,5-dihydrofuran in the presence of HRh(CO)(PPh₃)₃. The influence of the temperature, pressure, catalyst concentration, and the nature of the solvent on the conversion of dihydrofuran, the composition of aldehydes obtained and the selectivity of their formation was investigated.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2569–2571, November, 1989.     

Protolytic cleavage of derivatives of 2,5-dimethoxy-2,5-dihydrofuran

By analysis of the products from the protolytic cleavage of methyl 3-(2,5-dialkoxy-2,5-dihydro-2-furyl)propionate (I) in the presence of mixed nucleophiles and investigation of their mutual transformations the main paths in the dissociation of the protonated molecule of (I), with the formation of both linear cleavage products (derivatives of 1,4-diketones and 4-ketopimelic acid) and furylcarbinol derivatives, were determined.Latvian Institute of Organic Synthesis. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 190–197, February, 1997.     

Synthesis and Chemical Transformations of 2-imino-2,5-dihydrofurans

Chemistry of Heterocyclic Compounds - 2-Imino-2,5-dihydrofurans are a highly valuable class of heterocyclic compounds that show versatile biological activity and are used in diverse fields of...     

The synthesis of 2,5-dihydrofurans from α-allenic alcohols

α-Allenic alcohols react rapidly with PhSeCl to produce derivatives of 3-phenyl-seleno-2,5-dihydrofuran in high yields.     

Use of palladium-mediated allylic substitution reactions in the synthesis of 2,5-disubstituted-2,5-dihydrofurans

2,5-Disubstituted-2,5-dihydrofurans were synthesised in both one- and two-pot reactions starting from 2,5-diacetoxy-2,5-dihydrofuran. These palladium-mediated allylic substitution reactions were useful in preparing symmetrical or unsymmetrical products by employing the same nucleophile twice or two different nucleophiles, respectively.     

Enantiopure cis- and trans-2,5-disubstituted-2,5-dihydrofurans from d-allal- and d-galactal-derived vinyl epoxides

Upon treatment with the metal enolates of methylene active compounds (dimethyl malonate and dibenzoylmethane) (C-nucleophiles) and benzyl carbamate (N-nucleophile), d-allal- and d-galactal-derived vinyl epoxides are stereoselectively transformed, in a single step, into diastereoisomeric, highly functionalized, enantiopure cis- and trans-2,5-disubstituted-2,5-dihydrofurans.     

Gold(I)-catalyzed stereoselective formation of functionalized 2,5-dihydrofurans

[reaction: see text] A study concerning the gold(I)-catalyzed rearrangement of butynediol monobenzoates into functionalized 2,5-dihydrofurans is described. The mild reaction conditions employed allow the efficient and rapid stereoselective synthesis of a variety of 2,5-dihydrofurans via a sequence of two gold(I)-catalyzed isomerization steps.     

Synthesis of new unsaturated derivatives of functionally substituted 2-imino-2,5-dihydrofurans

5,5-Substituted 2-imino-4-methyl-2,5-dihydrofuran-3-carbonitriles reacted with aromatic aldehydes to give the corresponding 5,5-substituted 2-imino-4-(2-R-vinyl)-2,5-dihydrofuran-3-carbonitriles. The latter were converted into hydrochlorides which were hydrolyzed to 3-cyano-4-(2-R-vinyl)-2,5-dihydrofuran-2-ones whose condensation with malononitrile afforded dicyanomethylidene derivatives.     

Gold(III) chloride catalyzed cyclization of alpha-hydroxyallenes to 2,5-dihydrofurans

[reaction: see text] Functionalized alpha-hydroxyallenes 1 were smoothly converted into the corresponding 2,5-dihydrofurans 2 by using 5-10 mol % of gold(III) chloride as catalyst. This mild and efficient cyclization method can be applied to alkyl- and alkenyl-substituted allenes at room temperature, furnishing tri- and tetrasubstituted dihydrofurans in good to excellent chemical yields and with complete axis to center chirality transfer.     

Synthesis and some chemical transformations of novel functionalized 2-imino-2,5-dihydrofurans

Hitherto unknown functionalized 2-imino-3-(N-cyclohexylcarbamoyl)-2,5-dihydrofurans were synthesized by the reactions of tertiary α-hydroxy ketones with N-cyclohexyl(cyano-acetamide). Several reactions of thus synthesized compounds at the imino group were carried out.     

Synthesis of 2-alkyl- and aryl-3-ethoxycarbonyl-2,5-dihydrofurans through gold-catalyzed intramolecular hydroalkoxylation

Treatment of a wide range of functionalized hydroxyallenic esters with 5 mol % Ph(3)PAuCl and 5 mol % AgOTf in CH(2)Cl(2) at 25 °C for 1 h produced selectively 2-alkyl- and aryl-3-ethoxycarbonyl-2,5-dihydrofurans in good to excellent yield through intramolecular hydroalkoxylation by a 5-endo mode.