Computer-Assisted Design of Ionic Liquids for Efficient Synthesis of 3(2H)-Furanones: A Domino Reaction Triggered by CO₂

Abstract

A strategy for the highly efficient synthesis of 3(2H)-furanones by hydration of diyne alcohols catalyzed by base-functionalized ionic liquids under atmospheric-pressure CO that was developed through computer-assisted design is reported. The best range of basic ionic liquids as catalysts was predicted at first, and [HDBU][BenIm] exhibited the highest catalytic activity. Through a combination of NMR spectroscopic investigations and quantum-chemical calculations, the results indicated the importance of the basicity of the anion and the species of cation in the ionic liquid.

Ionic Liquids Catalysis for Carbon Dioxide Conversion With Nucleophiles

“…Subsequently, Wang and co-workers firstly realize ILs-catalyzed one-pot domino hydration of diyne alcohols to synthesize 3-(2H)-furanones (Figure S21 ), where H 2 O acts as both a substrate and solvent under atmospheric pressure CO 2 (Chen et al, 2016b ). This is the first time to predict the catalytic activity of ILs through quantum calculation, and [HDBU][BenIm] shows more effective on catalytic activity than other ILs.…”

Synthesis of Functionalized 5-Amino-3(2H)-furanones via Base-Catalyzed Ring-Cleavage/Recyclization of 4-Cyano-3(2H)-furanones in the Presence of Water

“…When R 1 substituents were biphenyl or naphthyl groups, 5-amino-3(2H)furanones 2g-m were formed in 40 minutes (entries 7-13). 5-Furanyl and 5-thienyl substituents of the 4-cyano-3(2Н)furanones 1n,o considerably reduced the reaction time and full conversion was achieved in 3 hours (entries 14,16). With the 4-cyano-3(2Н)-furanone 1q bearing a pyrrole ring, the corresponding product 2q was obtained in 24 hours (entry 18).…”

“…IR (KBr): 3359, 3310, 3097, 3057, 2990, 2943, 1629, 1594, 1491, 1448, 1368, 1346, 1310, 1259, 1238, 1209, 1154, 1129, 1067, 1029 . (11), 201 (14), 177 (17), 176 (38), 160 (30), 159 (100), 136 (37), 135 (17), 133 (11), 132 (14), 131 (10), 120 (45), 108 (19), 104 (16), 94 (49), 93 (31), 92 (29), 80 (14), 78 (10), 69 (28), 68 (19), 67 (19), 66 (29), 65 (59), 58 (12), 51 (10), 43 (12), 41 (36), 40 (11), 39 (45).…”

“…С NMR (100.6 MHz, CDCl 3 ): δ = 195.1 (C=O), 179.4 (C-5), 176.5 [C(O)-pyrrolyl], 137.0, 133.3 (C-pyrrolyl), 132.0, 129.0, 127.4, 124.6 (C 6 H 5 ), 117.7, 108.5 (C-pyrrolyl), 94.9 (C-4), 91.6 (C-2), 32.2, 24.3, 21.6 (C-cHex). 14, 143 (56), 141 (15), 140 (12), 138 (17), 115 (55), 114 (10), 109 (15), 108 (10), 81 (25), 79 (16).…”

Predicting the Toxicity of Ionic Liquids toward Acetylcholinesterase Enzymes Using Novel QSAR Models

“…With ever-increasing demand for clean energy and stricter environmental regulations, scientists have always strived for sustainable and green chemical products [1]. The apparent benefits of ionic liquids (ILs) has spurred intensive research in order to replace the conventional hazardous solvents for broad scale industrial applications, such as organic reaction [2,3,4,5,6,7,8], catalytic processes [9,10,11,12], gas separation [13,14,15,16], storage materials [17,18,19,20], etc. Among the unique properties of ILs, negligible vapor pressure has primarily attracted the attention of many researchers, and the field has sought improvements in positively affecting overall efficiency of many chemical processes under the principles of green chemistry [21,22].…”