Reactions of 5-aryl-3-arylmethylene substituted 3H-furan-2-ones and 3H-pyrrol-2-ones with acetoacetic ester

Structure, Z′ = 2 Crystal Packing Features of 3-(2-Chlorobenzylidene)-5-(p-tolyl)furan-2(3H)-one

“…Arylmethylidene derivatives are also available as scaffolds for the synthesis of various heterocyclic compounds of different complexity. These substances combine the properties of unsaturated carbonyl compounds and esters, allowing the implementation of reactions with various C-nucleophiles such as acetoacetic ester [ 18 ], acetylacetone [ 19 ], cyclohexanone [ 20 ], and mono- and N , N -binucleophiles [ 21 , 22 ]. Owing to the presence of a conjugated double bond, arylidene derivatives can easily add azides [ 23 , 24 ] oxygen (to give rise corresponding epoxides [ 25 ]), and halogen [ 26 ].…”

Synthesis of Compounds of the Pyrimidine Series Based on the Reactions of 3-Arylmethylidenefuran-2(3H)-ones with N,N-Binucleophilic Reagents

“…As a substrate, 3-arylmethylidenefuran-2(3 H )-ones have some advantages. They can be easily obtained, and they are convenient, cost-effective substrates for the synthesis of various hard-to-reach heterocyclic, spirocyclic, and polycyclic compounds [ 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 ]. 3-Arylmethylidenefuran-2(3 H )-ones are substances which combine the properties of internal esters and α,β-unsaturated carbonyl compounds, and they are able to react with substances with mobile hydrogen atoms.…”

Synthesis of 6-amino-4-aryl- 2R-4H-furo[2,3-b]pyran-5-carbo- nitriles based on the condensation of 3-arylmethylene-3H-furan-2-ones with malononitrile

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The ability of 3-arylmethylene-3H-furan-2-ones to take part in Michael condensation as acceptors was used earlier in the reaction with cyclohexanone [1], acetylacetone [2], and acetoacetic ester [3].In a continuation of investigations into the reactivity of 3-arylmethylene-3H-furan-2-ones with methylene-active compounds their behavior in reaction with malononitrile was studied.The presence of the highly reactive methylene and cyano groups in malononitrile makes it possible to use this compound as a reagent for cyclizations leading to the formation of carbo-and heterocyclic compounds.The reaction of 5-aryl-3-arylmethylene-3H-furan-2-ones 1-4 with malononitrile was realized by heating the reagents in solution in DMSO in a molar ratio of 1:1 in the presence of catalytic amounts of triethylamine.

1-4 5-8Et 3 N 1, 5 R = C 5 H 11 ; 2, 6 R = Ph; 3, 7 R = p-Tol; 4, 8 R = 3-MeOC 6 H 4

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“…The ability of 3-arylmethylene-3H-furan-2-ones to take part in Michael condensation as acceptors was used earlier in the reaction with cyclohexanone [1], acetylacetone [2], and acetoacetic ester [3].…”