Reaction between cyclohexy isocyanide, dialkyl acetylenedicarboxylates and 1-aryl-2-ene-3-acetyl-1,4-diketones. One-pot synthesis of highly functionalized 5-cyclohexylimino-2,5-dihydrofurans

Abstract

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 5cyclohexylimino-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.

Use of Dialkyl Acetylenedicarboxylates in the Multicomponent Synthesis of Heterocyclic Structures

“…[38] The three-component reaction of cyclohexyl isocyanide 12, dialkyl acetylenedicarboxylate 1 and 1-aryl-2ene-3-acetyl-1,4diketone derivatives 44 for the synthesis of 5-cyclohexylimino-2,5-dihydrofurans 45 was reported in 2018 by Latifi et al This approach was achieved in CH 2 Cl 2 at room temperature (Scheme 18). [39] Furanone derivatives 46 were synthesized using the threecomponent reaction of aniline 2, dialkyl acetylenedicarboxlate 2, Entry 2), [40] using tetra-methylguanidine-functionalized silica-coated iron oxide magnetic nanoparticles (Fe 3 O 4 @TMG) as an efficient catalyst in ethanol (Table 2, Entry 2), [41] in the presence of Al-droped ZnO nanostructure (0.025 g) in EtOH in refluxing and under ultrasonic irradiation at 70 °C (Table 2, Entry 3), [42] and also in the presence of silicacoated magnetic nanoparticles based on acidic ionic liquid in EtOH (Table 2, Entry 4). [43] A proposed possible mechanism for the synthesis of 46 is shown in Scheme 20.…”