89201-18-3

Upstream product

• 1074-12-0 phenylglyoxal hydrate 
• 123-54-6 acetylacetone 
• 43020-10-6 1-(2-methyl-5-phenyl-3-furanyl)ethanone 
• 52313-43-6 3-acetyl-1-phenyl-pentane-1,4-dione 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 1075-06-5 2,2-dihydroxy-1-phenyl-ethanone 
• 98-86-2 acetophenone 
• 90043-52-0 5-Acetyl-4-methyl-1-phenyl-2,3,7-trioxabicyclo<2.2.1>hept-5-ene 

Downstream Products

• 41398-19-0 3-methyl-6-phenylpyridazine 
• 1316302-66-5 1-(4-(1H-indol-3-yl)-2-methyl-5-phenylfuran-3-yl)ethanone 

Relevant academic research and scientific papers

Reactions of cyclohexyl isocyanide, dialkyl acetylenedicarboxylates and 1-aryl-2-ene-3-acetyl-1,4-diketones: One-pot synthesis of highly functionalized 5-cyclohexylimino-2,5-dihydrofurans

Dihydrofurans are important intermediates in organic synthesis, and are also important starting materials used in syntheses of a number of natural products. A facile synthesis of highly functionalized 5- cyclohexylimino-2,5-dihydrofuran derivatives by the multi-component reaction of cyclohexyl isocyanide, dialkyl acetylenedicarboxylates and 1-aryl-2-ene-3-acetyl-1,4-diketones is described.

Unexpected C-C bond cleavage: A route to 3,6-diarylpyridazines and 6-arylpyridazin-3-ones from 1,3-dicarbonyl compounds and methyl ketones

An unexpected C-C bond cleavage has been revealed in the absence of metal. This observation has been exploited to develop an efficient approach toward 3,6-diarylpyridazines and 6-arylpyridazin-3-ones from simple and commercially available 1,3-dicarbonyl compounds and methyl ketones.

Stereoselective synthesis of α-ylidene-β-dicarbonyl compounds: A mild PhI(OAc)2-mediated dehydrogenation process

PhI(OAc)2-mediated dehydrogenation of α-alkyl-β-dicarbonyl compound has been developed to afford α-ylidene-β- dicarbonyl compounds with high stereoselectivity under mild conditions. This process provides a complementary entry to stereoselectivity for the Knoevenagel reaction.

Formation of unsymmetrical 1,4-enediones via A focusing domino strategy: Cross-coupling of 1,3-dicarbonyl compounds and methyl ketones or terminal aryl alkenes

A highly efficient synthesis of unsymmetrical 1,4-enediones from 1,3-dicarbonyl compounds and methyl ketones or terminal aryl alkenes has been developed via a focusing domino strategy. Simple and readily available starting materials, mild reaction conditions, and a very simple operation are advantages of the reaction, which allow straightforward synthesis of a variety of unsymmetrical 1,4-enediones.

Synthesis of polyfunctionalized furans from 3-acetyl-1-aryl-2-pentene-1,4-diones

The BF3-catalyzed cyclization of 3-acetyl-1-aryl-2-pentene-1,4-diones 1a-e in the presence of water in boiling tetrahydrofuran gave bis(3-acetyl-5-aryl-2-furyl)methanes 2a-e in 26-79% yields along with a small amount of 3-acetyl-5-aryl-2-methylfurans 3a-e. The exact structure of 2a was determined by X-ray crystallography. The use of a half volume of the solvent for the reaction of 1a resulted in the formation of 2,4-bis(3-acetyl-5-phenyl-2-furfuryl)-3-acetyl-5-phenylfuran (4) together with 2a and 3a. A similar reaction of 1a was carried out in the presence of 3-acetyl-5-(4-methylphenyl)-2-methylfuran (3d) to afford 4-(3-acetyl-5-phenyl-2-furfuryl)-3-acetyl-5-(4-methylphenyl)-2-methylfuran (5) in 49% yield. The BF3-catalyzed reaction of 1a with 2,4-pentanedione in dry tetrahydrofuran at 23°C gave 3-(3-acetyl-5-phenyl-2-furfuryl)-4-hydroxy-3-penten-2-one (6a) and 3-(3-acetyl-2-methyl-4-phenyl-5-furyl)-4-hydroxy-3-penten-2-one (7a) in 66 and 24% yields, respectively. The product distribution depended on the reaction temperature. A similar reaction of 1b-e also yielded the corresponding trisubstituted furans 6b-e and tetrasubstituted furans 7b-e in good yields. These results suggested the presence of the furfuryl carbocation intermediate A during the reaction. The one-pot synthesis of 6a and 7a was also achieved by a similar reaction using phenylglyoxal. The deoxygenation of 1a with triphenylphosphine gave 3a in 88% yield, while 1a was treated with concentrated hydrochloric acid to yield 3-acetyl-2-chloromethyl-5-phenylfuran (8) which was quantitatively transformed in ethanol into 3-acetyl-2-ethoxymethyl-5-phenylfuran (9) and in water into 3-acetyl-5-phenylfurfuryl alcohol (10), respectively. In addition, the Diels-Alder reaction of cyclopantadiene with 1a gave the corresponding [4+2] cycloaddition products 11 and 12.

Photooxygenation of 3-acetyl-5-aryl-2-methylfurans via endoperoxide intermediate and the following reactions

The photooxygenation of 3-acetyl-5-aryl-2-methylfurans 1a-e selectively produced 2,2-diacetyl-3-aroyloxiranes 2a-e, 3-acetyl-1-aryl-2-pentene-1,4-diones 3a-e, and 3-acetyl-1-aryl-2-hydroxy-2-pentene-1,4-diones 4a-d via the endoperoxide intermediate A depending on the reaction conditions and the work-up procedure. The oxiranes 2a-e were mainly obtained in 56-77% yields by allowing the reaction mixture to stand at ambient temperature after the irradiation, while the treatment of the reaction mixture with water mainly gave the 1,4-diones 3a-e (62-69%). Heating the reaction mixture at 80°C after the irradiation decreased the total yield of the products, however, the enols 4a-d were newly formed in 8-12% yields. Direct UV irradiation of the endoperoxide intermediate A led to the homolytic fission of the peroxide linkage to produce the same enols 4a-e (16-39%). The self-sensitized photooxygenation of 1a-d using a UV light also gave 4a-d in a similar yield. The reaction pathway is discussed based on these results.

Acid-catalyzed convenient transformation of 1-aryl-2-pentene-1,4-diones into polyfunctionalized furans

The reaction of phenylglyoxal with 2,4-pentanedione in the presence of boron trifluoride gave the unstable 3-acetyl-1-phenyl-2-pentene-1,4-dione intermediate which was converted in situ by the reaction with an excess amount of 2,4-pentanedione into new crystalline tri- and tetra-substituted furans. Other unstable 1-aryl-2-pentene-1,4-diones, which were obtained by the photooxygenation of 3-acetyl-5-aryl-2-methylfurans, were trapped by the acid-catalyzed reaction, giving polyfunctionalized furans in good yields. Treatment of the 1-phenyl-2-pentene-1,4-dione intermediate with concentrated hydrochloric acid followed by boiling ethanol quantitatively yielded a stable 2-ethoxymethylfuran via the unstable 2-chloromethylfuran. (C) 2000 Elsevier Science Ltd.