Five-membered ring systems with one heteroatom: Synthetic routes, chemical reactivity, and biological properties of furan-carboxamide analogues

ABSTRACT

This review described the synthetic methods, chemical reactivity and biological applications of furan carboxamide compounds. Furan-carboxamides are reported to have important and variable biological properties. The aim of this review is to highlight the chemistry and biological importance of this class of bioactive compounds. The basic sections covers: structure studies, synthetic methods pathways, synthesis of different heterocycles, reactions and biological applications. The reactions mechanisms of the unexpected products are discussed. The present study covers all the published work on the furan-carboxamides until now.

GRAPHICAL ABSTRACT

KEYWORDS:

• Biological importance
• chemical reactivity
• furan-carboxamides
• synthetic applications

Abbreviations:

• 5-HT1A: 5-hydroxytryptamine receptor gene
• AgBF₄: silver tetrafluoroborate
• CDI: N:N’-carbonyldiimidazole
• CH₂Cl₂: dichloromethane
• Cu(OTf)₂: copper(II) triflate
• DCC: 1:3-dicyclohexylcarbodiimide
• DEPC: diethyl pyrocarbonate
• DHOBt: 3:4-dihydro-3-hydroxy-1:2:3-benzotriazin-4-one
• DIPEA or DIEA: N:N-diisopropyl ethylamine or Hünig’s base
• DMAP: trifluoromethyl-sulfonyl-N:N-dimethylaminopyridine
• DNA: deoxyribonucleic acid
• EDAC: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride
• Et₃SiH/F₃B-OEt₂: triethylsilane/boron trifluoride–diethyl ether
• HIV-1: human immunodeficiency virus type 1
• LAH: lithium aluminum hydride
• LDA: lithium diisopropylamide
• NMR: nuclear magnetic resonance
• PCy₃·HBF₄: tricyclohexylphosphine tetrafluoroborate
• Pd(OAc)₂: palladium(II) acetate
• POCl₃: phosphorus oxychloride
• rt: room temperature
• Ru: ruthenium
• t-BuOK: potassium tert-butoxide
• Tf₂O: trifluoromethanesulfonic anhydride
• THF: tetrahydrofuran