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

Abstract

2H)-Furanones are a type of five-membered heterocyclic compounds of synthetic and biological importance. For exploring the utilities of this ''sweet'' aroma component for bio-analytical purposes we have prepared and characterized two novel fluorophores (2Z)-2-(5-fluoro-2-ntro benzylidene)-5phenyl-3(2H)-furanone (FNPF) and (2Z)-2-(4-carboxy benzylidene)-5-phenyl-3-(2H)-furanone (CBPF) on a 3-furanone skeleton. In order to expand their application potential, the photophysical properties have been investigated using absorption and emission spectroscopy, in combination with quantum chemical calculations. As expected, both compounds showed efficient solvatochromic properties and the excited state dipole moments are larger than those of the ground state. Solvent dependent spectral data using TD-DFT calculations on the optimized ground and excited state structures of both compounds were found to correlate well with the experimental findings.Scheme 1 Reaction conditions: (a) NH 2 OHÁHCl, NaOH, stirring; (b) N(CH 2 CH 3 ) 3 , propargyl alcohol, NaOCl, stirring in an ice bath; (c) H2, Pd/ C; (d) H + , NaHCO 3 .

Synthesis of 3(2H)‐Furanones: A Review

“…Suliman and co‐workers reported the synthesis of 5‐substituted‐3(2 H )‐furanone starting from benzaldehyde (Scheme 10). [ 15 ] The synthetic route involving three steps commenced with the conversion of benzaldehyde to benzaldoxime 47 from which 3‐phenyl‐5‐(isoxazolyl) methanol 48 was prepared by a 1,3‐diploar cycloaddition with propargyl alcohol. The substituted isoxazole was subjected next to catalytic hydrogenation with 10 % Pd/C as catalyst and subsequent acidic hydrolysis furnished 5‐phenyl‐3(2 H )‐furanone 50 in 62 % yield.…”

Synthesis of 5-Aryl-3(2H)-furanones Using Intramolecular Cyclization of Sulfonium Salts

“…16 1.41 g, 93% yield; orange oil; R f = 0.56 (n-hexane/EtOAc = 2:1); IR (neat): 1614, 1469, 760 cm −1 ; 1 H NMR (500 MHz, CDCl 3 ) (enol form): δ 7.57 (dd, J = 1.6, 0.8 Hz, 1 H), 7.15 (dd, J = 3.5, 0.8 Hz, 1 H), 6.55 (dd, J = 3.5, 1. 6 form): δ 189. 5, 176.2, 150.5, 145.9, 115.5, 112.4, 96.1, 25.4 500MHz, CDCl 3 ) (enol form): δ 7.69 (dd, J = 3.8, 1.1 Hz, 1 H), 7.60 (dd, J = 4.9, 1.1 Hz, 1 H), 7.13 (dd, J = 4.9, 3.8 Hz, 1 H), 6.03 (s, 1 H), 2.14 (s, 3 H); 13 C{ 1 H} NMR (126 MHz, CDCl 3 ) (enol form): δ 187.…”

“…5 In addition, 5-aryl-3(2H)furanones can be used as scaffolds for the synthesis of fluorescent organic dyes. 6 Most of the synthetic methods available for 5-aryl-3(2H)-furanones are used to produce 2,2disubstituted 5-aryl-3(2H)-furanones, and there are very few methods for synthesizing 5-aryl-3(2H)-furanones that are unsubstituted at the 2-position of the 3(2H)-furanone ring. A few synthetic methods of 5-phenyl-3(2H)-furanone are reported, for example, the procedure including hydrogenation of isoxazole, followed by intramolecular cyclization (Scheme 1a).…”

One‐pot two‐step synthesis of fused thiazinofuranone linked geminal bis 1,2,3‐triazole hybrids and their in vitro cytotoxic screening

“…Furanones and their fused frameworks are versatile heterocyclic moieties that exist in many natural products [1,2] and biologically active compounds [3]. In particular, 2,2-di substituted furanone core is present in many natural products such as Pseurotin A [4], Hyperolactone C [5,6], Trachyspic acid [7,8], Jatrophone [9], Eremantholide A [10], Cephalimysin A [11], Geiparvarin [12,13], Bullatenone [14] Griseofulvin [15] and have been discovered to possess a broad range of medicinal applications [3] and also used for the synthesis of fluorescent materials [16].…”