Hybrid hetarylhydrazones and enamines of Furan-2(3H)-ones as a framework for the synthesis of poly-N-heterocycles

Abstract

Substituted furan-2(3H)-ones can act as platform compounds to obtain easily various functionalized derivatives as well as heterocycles with different heteroatoms patterns. In this study, we suppose a simple and effective way to reach poly-N-heterocycles using a set of hybrid hetarylhydrazones and enamines based on furan-2(3H)-ones as a starting material. The presence of a few reaction centers in these the hybrid furan-2(3H)-one derivatives allows them to undergo some intramolecular rearrengements with opening furan ring as well as with keeping it unaffected followed by the increase of complexity of the resulting heterocycles, depending on reaction conditions. It was found that the reaction conditions and the nature of the substituents in the hydrazone fragment affect the direction of the interaction and the nature of the resulting products. Different approaches form a framework which allowed us to create a library of substituted annelated poly-N-heterocycles with highly prominent biological effects. Analysis of the possible biological effects was performed in silico which allows us to reveal leading structures among all synthesized compounds.

Keywords

• Hetarylhydrazones
• Enamines
• Furan-2(3H)-one
• Intramolecular cyclocondensation
• Poly-N-heterocycles