Copper-Catalyzed [4 + 1] Annulation between α-Hydroxy Ketones and Nitriles: An Approach to Highly Substituted 3(2H)-Furanones

Abstract

A copper-catalyzed [4 + 1] annulation between α-hydroxy ketones and nitriles has been developed. The reaction provides a facile and efficient method for the construction of a wide range of highly substituted 3(2H)-furanones, a class of important compounds known to be associated with several biological activities.

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

“…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).…”

“…12 In the light of the above importance of 3(2H)-furanones, it is of great interest to develop an easy access to a variety of these molecules. Different synthetic routes have been used for the preparation of 3(2H)-furanones, including an acidor base-catalyzed cyclization/dehydration reaction of 1-hydroxy-2,4-diketones, 7a,13 the hydrogenolysis and subsequent acidic hydrolyses of isoxazoles, 8b the aldol reaction of 3-silyloxyfuranes, 14 condensation of R-acyloxycarbonyl compounds, 3d,15 ionic liquid-catalyzed hydration of diyne alcohols triggered by CO 2 , annulation between α-hydroxy ketones and nitriles, 17 intramolecular cyclization of sulfonium salts, 18 and quinine-catalyzed Michael/O-alkylation reaction of maleimides with γ-halogenated-β-keto esters. 19 In addition, cyclization of acetylenic ketones 20 to 3(2H)-furanones in the presence of Au(III), Ag(I), Cu(I), Hg(II), Pd(II), or Pt(II) has also been described.…”

“…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).…”

3(2H)-Furanone as a promising scaffold for the synthesis of novel fluorescent organic dyes: an experimental and theoretical investigation

“…[13][14][15][16][17][18][19][20][21] Although a number of synthetic approaches for 3(2H)-furanones were known they were in many cases limited to specific substitution patterns. [13][14][15][16][17][18][19][20][21] Although a number of synthetic approaches for 3(2H)-furanones were known they were in many cases limited to specific substitution patterns.…”

Synthesis of Substituted 3(2H)-Furanones Using Alkylative Intramolecular Cyclization of Sulfonium Salts

“…Finally, the reactions were attempted using sulfonium salts 1 bearing various ester moieties and benzyl bromide and the desired products was obtained in moderate to good yields (entries [15][16][17][18][19][20][21][22]. It should be emphasized that a variety of 4-alkylated 3(2H)-furanones were readily obtained in moderate to good yields by simple one-pot process.…”