Silica-Supported Alginic Acid-L-Glutamic Acid: An Efficient Heterogeneous Catalyst for Solvent-free Synthesis of 1,8-Dioxohexahydroacridine and Polyhydroquinoline Derivatives

Sharzad Javanshir,Mohammad Dekamin,Mohammad Farhadnia,Mahsa Yarhosseini

doi:10.3390/ecsoc-18-a015

Abstract

4-Substituted 1,4-dihydropyridine (1,4-DHP) nucleus is a fertile source of biologically important molecules possessing various important pharmacological properties such as antihypertensive, anti-therosclerotic, hepto-protective, anti-mutagenic, vasodilator, bronchodilator, antitumor, geroprotective and anti-diabetic agents. Thus, these compounds are analogues of NADH coenzymes, which have been investigated for their calcium channel activity and the heterocyclic rings are found in variety of bioactive compounds. Therefore we report herein a convenient and environment-friendly approach for the synthesis of biologically active substituted Hantzsch 1,8-dioxohexahydroacridine and polyhydroquinoline derivatives via a one-pot pseudo four component reaction of various aldehydes, ammonium acetate, cyclic 1,3-dicarbonyl compounds and ethyl acetoacetate in the presence of silica-supported alginic acid-L-glutamic acid (SiO2-AA-L-Glu) as a new, heterogeneous and essential catalyst is reported under solvent-free conditions at 100 °C. In recent years heterogeneous catalysts have attracted a great attention due to efficiency, and for economic and environmental reasons. SiO2-AA-L-Glu has been prepared by a simple method to act as a efficient catalyst with high catalytic activity and reusability for the synthesis of biologically active substituted Hantzsch derivatives under thermal condition. The proposed methodology is suitable for producing the desired products in good to excellent yields with short reaction time and straightforward workup.

Highlights

The classical Hantzsch reaction is one of the simplest and most economical methods for the synthesis of biologically important and pharmacologically useful 1,4-dihydropyridine derivatives
The utilization of cyclic 1,3-diketone in Hantzsch reaction for the synthesis of polyhydroquinoline and 1,8-dioxohexahydroacridine was recently demonstrated by using molecular iodine [9], ionic liquids [10,11], iodotrimethylsilane (TMSI) [12], organocatalysts
In continuation with our research devoted to the development of green organic chemistry we report a facile and efficient synthesis of this derivatives via a one-pot, fourcomponent Hantszch condensation of 1,3-dicarbonyl compound, aldehydes, ethyl acetoacetate and ammonium acetate using a catalytic amount of SiO2-AA-L-Glu as a new, heterogeneous and essential catalyst under solvent-free conditions at 100 °C

Summary

Introduction

The classical Hantzsch reaction is one of the simplest and most economical methods for the synthesis of biologically important and pharmacologically useful 1,4-dihydropyridine derivatives. In 1882, Arthur Hantzsch [8] reported the first synthesis of symmetrical substituted 1,4-dihydropyridines via multi-component condensation of aldehyde, ethylacetoacetate and ammonia in acetic acid or refluxing alcohol. In continuation with our research devoted to the development of green organic chemistry we report a facile and efficient synthesis of this derivatives via a one-pot, fourcomponent Hantszch condensation of 1,3-dicarbonyl compound, aldehydes, ethyl acetoacetate and ammonium acetate using a catalytic amount of SiO2-AA-L-Glu as a new, heterogeneous and essential catalyst under solvent-free conditions at 100 °C (scheme 1).

Results

Conclusion