A facile strategy for the one pot multicomponent synthesis of spiro dihydropyridines from amines and activated alkynes

Efficient Synthesis of the Functionalized Spiro[indoline‐3,4′‐pyridine] via Four‐component Reaction

“…The reactions of α-naphthylamine and benzylamine also resulted in the spiro compounds 1i and 1j in good yields. [31] To explain the formation of spiro[indoline-3,4'-pyridine] from this one-pot multicomponent reaction, a plausible reaction mechanism was proposed based on our recently reported four-component reaction for the synthesis of 1,4-dihydropyridines [26] The structures of thirteen prepared spiro[indoline-3,4'-pyridines] 1a-1m were fully characterized by elemental analysis, 1 H NMR and 13 C NMR, MS, IR spectra, and were further confirmed by single-crystal X-ray diffraction study performed for compound 1l (Figure 1).…”

“…[1][2][3][4] Their potential properties have prompted many efforts toward the synthesis of spirooxindole-fused heterocycles. [10][11][12][13][14][15][16][17][18][19][20][21] Recently multicomponent reactions based on the sequential reactions of isatins [22,23] or benzofuran-2,3-diones [24,25] with Huisgen's 1,4-dipoles, which were formed in situ from the addition of azaarenes with electron-deficient alkynes have been successfully used to construct versatile spirooxindole systems. [10][11][12][13][14][15][16][17][18][19][20][21] Recently multicomponent reactions based on the sequential reactions of isatins [22,23] or benzofuran-2,3-diones [24,25] with Huisgen's 1,4-dipoles, which were formed in situ from the addition of azaarenes with electron-deficient alkynes have been successfully used to construct versatile spirooxindole systems.…”

Molecular diversity of spirooxindoles. Synthesis and biological activity

“…A novel synthetic strategy was realized for the formation of the chiral spiropiperidineoxindole system 276 from a ring closing metathesis of an enantiopure quaternary 3-aminooxindole 274 in the presence of a 2 nd generation Grubbs catalyst (Scheme 78) [164].…”

Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione

“…The various biological activities of spirooxindole derivatives have attracted much attention from organic chemists, and as a consequence, a number of methods have been reported for the preparation of spirooxindole-fused heterocycles [3–6]. Isatin and its derivatives may be the most useful starting materials or precursors in the synthesis of a wide number of spirocyclic oxindoles [7–8].…”