One‐Pot Synthesis of Spirooxindole Derivatives Catalyzed by Lipase in the Presence of Water

Abstract

A facile one-pot synthesis route to spirooxindole derivatives was developed by combining the three types of catalytic activities of lipase from porcine pancreas (PPL) in the presence of water, i.e., the Knoevengel condensation, Michael addition and cyclization. PPL showed excellent catalytic activity and have a good adaptability to different substrates in the reaction. All the reactions go smoothly and provide spirooxindole derivatives with high yield under the mild conditions. This lipase-catalyzed multistep conversion method has provided a new strategy to synthesize spirooxindole derivatives and expanded the application of biocatalysts.

An Efficient and Easy Method for the One‐pot Synthesis of Spirooxindoles in the Presence of Na2CO3

“…Tan white solid; mp 257–259°C (reported 260–262°C) ; FTIR (cm −1 ): 3479, 3155, 2978, 2189, 1678, 1595, 1467, 1381, 1286, 1211, 1070, 754, 678; 1 H‐NMR (400 MHz, DMSO‐ d 6 ): δ 0.80 (t, 3H, J = 1.6 Hz), 2.32 (s, 3H), 3.72 (m, 2H), 6.79 (d, 1H, J = 7.6 Hz), 6.9 (t, 1H, J = 7.2 Hz), 7.05 (d, 1H, J = 7.2 Hz), 7.14 (br s, 2H, NH 2 ), 7.16 (m, 1H), 10.39 (s, 1H, NH); 13 C‐NMR (100 MHz, DMSO‐ d 6 ): δ 13.4, 19.0, 49.4, 57.0, 60.7, 105.1, 109.8, 117.9, 122.3, 123.9, 129.0, 135.0, 142.6, 158.9, 159.4, 164.9, 179.0; Anal . Calcd.…”

Synthesis of spirooxindole pyrimidines catalyzed by silica-bonded N-propyltriethylenetetramine as a recyclable solid base catalyst in aqueous medium

“…Known compounds were characterized by comparison of their IR, 1 H NMR, and 13 C NMR spectroscopic data and their melting points with reported values [4,5,[44][45][46][47][48][49][50][51][52][53][54][55].…”

“…Among them, the one-pot condensation reaction of isatin and activated methylene reagent could readily afford various spirooxindole pyramidine structures and has attracted wide attention, and this type of reaction has been achieved by a number of different catalysts and conditions, such as InCl 3 [43], electrochemical methods [44], triethylbenzylammonium chloride (TEBA) [45], Et 3 N [46], tetrabutylammonium fluoride (TBAF) [47], NH 4 Cl [48], lipase [4], p-TSA [49], ZnS nanoparticles [50], NaCl under sonication [51], butylmethylimidazolium tetrafluoroborate ([BMIm]BF 4 ) [52], amino-functionalized SBA-15 [53], CaCl 2 under ultrasonic irradiation [54], piperidine under ultrasonic irradiation [55], nanocrystalline MgO [56], gluconic acid [57], MnFe 2 O 4 nanoparticles [58], 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU) [59], ethylenediammonium diformate (EDDF) [60], and sulfated choline based heteropolyanion [61] which some of them suffer from technical intricacy and generation of mixtures of pyrans and unsaturated nitriles.…”

“…Spirooxindoles are commonly occurring heterocyclic ring systems and are important structural motifs found in many natural products and pharmaceuticals [1][2][3][4][5] (Fig. 1).…”

A Novel Enzymatic Synthesis of Quinoline Derivatives

“…As part of our continued interest in enzymatic synthesis and exploring new synthetic approaches to quinoline derivatives [21,22], we herein report a novel, mild, and efficient preparation of quinoline derivatives using catalytic enzymes as shown in Scheme 1.…”