A series of spirooxindole tetrahydrofuran derivatives 3 were obtained in moderate to good yields via oxindole derivatives 1 and β-arylacrylonitrile derivatives 2via base-mediated cascade [3 + 2] double Michael reactions under mild conditions and the application of this method in the synthesis of bioactive analogues, such as functionalized spirooxindole octahydrofuro[3,4-c]pyridine derivatives 4 which contain two new heterocyclic rings and two quaternary carbon centers, has also been developed. Subsequently, antifungal activities of all of the synthesized compounds were evaluated against five phytopathogenic fungi (Rhizoctonia solani, Fusarium semitectum, Alternaria solani, Valsa mali and Fusarium graminearum) using the mycelium growth rate method. The preliminary results showed that the spirooxindole octahydrofuro[3,4-c]pyridine derivative 4 showed higher growth inhibition of Valsa mali and Fusarium graminearum, than spirooxindole tetrahydrofuran derivatives 3. For example, spirooxindole octahydrofuro[3,4-c]pyridine derivative 4ab, having a bromine atom at the meta position of the benzene ring, was the best compound in inhibiting F. g. with an IC50 value of 3.31, in particular with inhibition of 4ab on F. g. being similar to that of the control cycloheximide (IC50 = 3.3 μg mL−1).

A novel copper catalyzed domino three-component decarboxylative coupling and cyclization reaction using cyclic α-amino acids has been developed. This reaction provides an efficient and atom economic approach to 2-(2-indolyl)pyrrolidine, and 2-(1,1-dioxido-2H-benzo[e][1,2]thiazin-3-yl)pyrrolidine derivatives.

Solvothermal reactions of 4-cyanobenzoic acid (HL1), NaN3, hydrated ZnSO4 in the presence of ancillary ligands pyrazine or 4,4′-dimethylbipyridine (Me2bpy) afforded a 3-D coordination polymer [Zn(L2)(H2O)]n (1) and a 2-D layer [Zn3(Me2bpy)(N3)2(L2)]n (2) (L2 = 4-tetrazolylbenzenecarboxylate), respectively in which pyrazine significantly alters the self-assembly of 1 and the coordination of Me2bpy in 2 leads to a novel linearly trinuclear [Zn3(Me2bpy)2(N3)2]4 + subunit functioning as a secondary building block (SUB). Their crystal structures have been determined by X-ray crystallography and solid state luminescent properties have been measured at room temperature.Solvothermal reactions of 4-cyanobenzoic acid (HL1), NaN3, hydrated ZnSO4 in the presence of pyrazine or 4,4-dimethylbipyridine (Me2bpy) afforded complexes [Zn(L2)(H2O)]n (1) and [Zn3(Me2bpy)(N3)2(L2)]n (2), respectively in which pyrazine alters the self-assembly of 1 and the coordination of Me2bpy in 2 leads to a linearly trinuclear [Zn3(Me2bpy)2(N3)2]4+ subunit as a SUB.Highlights► Pyrazine significantly alters the self-assembly of 1 ► The novel [Zn3(Me2bpy)2(N3)2]4+ cores functions as the SUBs in 2 ► A 44 grid topological architecture with grid length of 12.5 Å in 2 is generated ► The luminescence properties have been measured.

A series of spirooxindole tetrahydrofuran derivatives 3 were obtained in moderate to good yields via oxindole derivatives 1 and β-arylacrylonitrile derivatives 2via base-mediated cascade [3 + 2] double Michael reactions under mild conditions and the application of this method in the synthesis of bioactive analogues, such as functionalized spirooxindole octahydrofuro[3,4-c]pyridine derivatives 4 which contain two new heterocyclic rings and two quaternary carbon centers, has also been developed. Subsequently, antifungal activities of all of the synthesized compounds were evaluated against five phytopathogenic fungi (Rhizoctonia solani, Fusarium semitectum, Alternaria solani, Valsa mali and Fusarium graminearum) using the mycelium growth rate method. The preliminary results showed that the spirooxindole octahydrofuro[3,4-c]pyridine derivative 4 showed higher growth inhibition of Valsa mali and Fusarium graminearum, than spirooxindole tetrahydrofuran derivatives 3. For example, spirooxindole octahydrofuro[3,4-c]pyridine derivative 4ab, having a bromine atom at the meta position of the benzene ring, was the best compound in inhibiting F. g. with an IC50 value of 3.31, in particular with inhibition of 4ab on F. g. being similar to that of the control cycloheximide (IC50 = 3.3 μg mL−1).