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

Abstract

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

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.…”