Synthesis and spectral properties of 3-furyl-4-hydroxycoumarins

Abstract

UDC 547. and Together with various chromone derivatives, their structural isomers --coumarins --are widely distributed in the plant world. Great interest in the study of coumarin compounds appeared with the detection of an anticoagulant action of 4-hydroxycoumarin and it increased in the following decades in connection with the discovery of many coumarin derivatives having hypothermal, anthelmintic, hypotensive, antimicrobial, diuretic, insecticidal, and vasodilatory actions and the possibility of their use as effective drugs (dicoumarol, novobiocin, nafarin, etilendikumarin, propenan, nitrofarin, ksilokumarol, and many others) in various diseases.Coumarin compounds with aryl substituents in position 3 are rarely encountered among substances of plant origin. Coumarins containing heterocyclic residues in this position are not found in nature. They can be obtained synthetically.Recently, intensive investigations on the synthesis and study of the chemical and biological properties of heterocyclic coumarin derivatives have been pursued in many laboratories [1], and compounds with interesting biological activities have already been found among them.In order to study their chemical and biological properties and to find new highly effective drugs among heterocyclic coumarin derivatives, we have synthesized derivatives of 4-hydroxycoumarin by the scheme given below. The synthesis was achieved under the conditions of the Claisen condensation with sodium tert-butanolate as catalyst. The 3-furyl-4-hydroxycoumarins obtained consisted of yellow crystalline substances readily soluble in the majority of organic solvents. They possessed a powerful characteristic fluorescence both in solutions and in the crystalline state.

An overview on synthesis and reactions of coumarin based compounds

“…-(5-Ethoxycarbonyl-2-furyl)-6-ethyl-4-hydroxy-7-methoxycoumarin (34) was prepared via Claisen condensation of α-(5-ethoxycarbonyl-2-furyl)-5-ethyl-2-hydroxy-4-methoxyacetophenone (32) in dry diethyl carbonate in the presence of sodium tert-butanolate in an atmosphere of argon to afforded hydroxycoumarins (33a-c), which were acylated affording hydroxycoumarins (34 a-I) (Fig.15) 33. …”

The Synthesis of 2-(Chromon-2/3-yl)-3-(5-thione-4-hydro-1,3,4-thiadiazol-2-yl)-4-oxo-thiazolidine

“…In the 1 H NMR spectra, the chemical shift of 2-H in chromones appeared at d 6-8, 8 but the 2-H in compounds 3a-3f appeared at about d 8.6. It was possible that the deshielding effect of an electron-withdrawing group linked in the 3-site led the chemical shift of 2-H in these compounds toward a downfield shift.…”

Extending the Inhibition Profiles of Coumarin-Based Compounds Against Human Carbonic Anhydrases: Synthesis, Biological, and In Silico Evaluation

“…Coumarins 9 and 10 (Figure 1) were synthesized according to the literature procedures [34,35]. Compounds 11 , 12 (Figure 1) were purchased and included in the CA inhibition assays.…”

“…Compounds 9 [34], 10 [35] were synthesized according to the literature procedures. Compounds 11 , 12 were purchased from InterBioscreen (Chernogolovka, Russia, ).…”