Furan-2 -ones synthesis

A. Tanaka and K. Yamashita, A novel synthesis of (/ )- and (S)-4-hydroxytetrahydro-furan-2-ones, Synthesis, 570 (1987). 

Furfural — see Furan-2-oarbaldehyde, 532 Furfuryl acetate, o -(butoxycarbonyl)-anodic oxidation, 1, 424 Furfuryi acrylate polymerization, 1, 279 Furfuryl alcohol configuration, 4, 544 2-Furfuryl alcohol polyoondensation, 1, 278 reactions, 4, 70-71 Furfuryl alcohol, dihydro-pyran-4-one synthesis from, 3, 815 Furfuryl alcohol, tetrahydro-polymers, 1, 276 rearrangement, 3, 773 Furfuryl chloride reactions... 

The reaction appears to be general and the additions are regiospecific and stereoselective. The product from the reaction with 2-propanol has been used for the synthesis of cis-chrysanthemic acid,8 and the product with methanol has been used for the construction of novel 2, 3 -dideoxy-3 -hydroxymethylnucleosides.9 In addition, ethane-1,2-diol provides the expected photoadduct as a 1 1 mixture of the two possible diastereoisomers, and these can be easily separated as their acetonides, to provide compounds with three contiguous chiral centers emanating from furan-ones with only one chiral center.9 More recently, we have shown that photoinduced-... 

Scheme 7. Synthesis of Furan(one) Derivatives from Hydroxyalkylation Product 1741176 obtained from Cyclopropane 162...

Scheme 10. Synthesis of Different Furan(one) Derivatives from a Siloxycyclopropane and Acetone...

Photocatalyzed Addition of Methanol to (5S)-5-0-tert-Butyldimethyl-siloxymethyl-furan-2(5H)-one Synthesis of (4R,5S)-4-Hydroxy-methyl-5-0-tert-butyldimethylsiloxymethyl-furan-2(5H)-one. 

F.H. Kohnke and co-workers prepared novel heterocyclophanes from cyclic poly-1,4-diketones, which were obtained by the oxidation of calix[6]furan and calix[4]furan. " One of the heterocyclophanes, calix[6]pyrrole, was prepared by the Paal-Knorr pyrrole synthesis from the corresponding dodecaketone. The substrate was heated with excess ammonium acetate in absolute ethanol. Interestingly, the analogous synthesis of calix[4]pyrrole under identical conditions failed, while calix[5]pyrrole is obtained only in 1% yield. 

Other interesting methods can generate furans. One method treats an allylic diol such as 125 with pyridinium chlorochromate (PCC see Chapter 17, Section 17.2.3), in an oxidative-cyclization process, to give 3-ethylfuran, 126. Thiophene derivatives can also be prepared from 1,4-dicarbonyl compounds. A Paal-Knorr thiophene synthesis reacts 2,4-hexanedione (115) with phosphorus pentasulfide (P4S10) to give 2,5-dimethylthiophene, 127. 

Chem Pharm Bull 31(9) 3160-3167. doi 10.1248/cpb.31.3160 Lefebvre Y (1972) Oxidation of furans. I. synthesis of 6-hydroxy-2H-pyran-3(6H)-ones. 

The proposed mechanism by which chlorinated dioxins and furans form has shifted from one of incomplete destmction of the waste to one of low temperature, downstream formation on fly ash particles (33). Two mechanisms are proposed, a de novo synthesis, in which PCDD and PCDF are formed from organic carbon sources and Cl in the presence of metal catalysts, and a more direct synthesis from chlorinated organic precursors, again involving heterogeneous catalysis. Bench-scale tests suggest that the optimum temperature for PCDD and PCDF formation in the presence of fly ash is roughly 300°C. 

H-Benzo[a]carbazole, 4,4a,5,l 1,1 la,l Ib-hexahydro-synthesis, 4, 283 Benzo[b]carbazole, N-acetyl-photochemical rearrangements, 4, 204 Benzo[/]chroman-4-one, 9-hydroxy-2,2-dimethyl-synthesis, 3, 851 Benzochromanones synthesis, 3, 850, 851, 855 Benzochromones synthesis, 3, 821 Benzocinnoline-N-imide ring expansion, 7, 255 Benzocinnolines synthesis, 2, 69, 75 UV, 2, 127 Benzocoumarins synthesis, 3, 810 Benzo[15]crown-5 potassium complex crystal stmcture, 7, 735 sodium complex crystal stmcture, 7, 735 Benzo[ 18]cr own-6 membrane transport and, 7, 756 Benzo[b]cyclohepta[d]furans synthesis, 4, 106 Benzocycloheptathi azoles synthesis, 5, 120... 

Benzo[b]furan-4(5H)-one, 6,7-dihydro-synthesis, 4, 710 Benzofuranones H NMR, 4, 579 Benzo[b]furanones from 3-hydroxyflavanone, 3, 729 Benzo[b]furan-2(3H)-ones — see 2-Coumaranones Benzo[b]furan-3(2H)-ones IR spectra, 4, 590 reactions, 4, 650 Benzo[ c]furan-1 (3 W) -ones carbanions, 4, 579 H NMR, 4, 579 reactions with arynes, 1, 415 structure, 4, 552... 

Furan-2(3H)-one, 4,5-dihydro-5-methyl-dipole moments, 4, 556 Furan-2(3H)-one, 5-methyl-reactions, 4, 648 Furan-2(5H)-one, 5-alkoxy-synthesis, 4, 135 Furan-2(5H)-one, 5-ethyl-synthesis, 4, 135... 

Phthalides — see Benzo[c]furan-l (3H)-one Phthalimide, 2-amino-pyridazine synthesis from, 3, 53 Phthalimide, N-cyclohexylthio-as vulcanization accelerator, 1, 404 Phthalimide. methylidine-polymerization, 1, 273 Phthalimide, N-(trichloromethylthio)-biocide, 1, 399 Phthalimide, 1-vinyl-polymerization, 1, 273 Phthalimide, N-vinyl-copolymer... 

Thieno[3,4-d][l,3]dithiol-2-one, 1-nitro-synthesis, 6, 1013 Thieno[3,4-c]furan, 4,6-dichloro-synthesis, 6, 1013 Thieno[3,4-c]furan, tetraphenyl-formation, 4, 1060 synthesis, 4, 1060 UV spectra, 4, 1044 Thieno[3,2-6]furans structure, 4, 1039 synthesis, 6, 1020 Thieno[3,4-c]furans... 

Several modifications of the Feist-Benary furan synthesis have been reported and fall into two general classes 1) reactions that yield furan products 2) reactions that yield dihydrofuran products. One variant that furnishes dihydrofiirans uses substrates identical to the traditional Feist-Benary furan synthesis with a slight modification of the reaction conditions. The other transformations covered in this section involve the combination of P-dicarbonyls with reagents that are not simple a-halocarbonyls. Several reactions incorporate a-halocarbonyl derivatives while others rely on completely different compounds. 

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