Caffeine as a naturally green and biodegradable catalyst promoted convenient and expedient synthetic route for the synthesis of polysubstituted dihydro-2-oxypyrroles

F Mohamadpour

doi:10.4314/bcse.v33i1.15

Abstract

A green, convenient, high yielding and one-pot procedure for synthesis of high substituted dihydro-2-oxypyrroles by domino four-component condensation reaction between aromatic/aliphatic amines, dialkyl acetylenedicarboxylate and formaldehyde in the presence of a catalytic amount of caffeine as a green, natural, expedient and biodegradable catalyst under ambient temperature was studied. The salient features of this green approach are simplicity of operation and work-up procedures with no necessity of chromatographic purification steps, use of safe, non-volatile, non-corrosive and green catalyst, the availability and easy to handle of this solid catalyst, one-pot reaction, economical and clean synthesis. KEY WORDS: Caffeine, Green catalyst, Polysubstituted dihydro-2-oxypyrroles, Ambient temperature, Simple work-up Bull. Chem. Soc. Ethiop. 2019, 33(1), 149-158DOI: https://dx.doi.org/10.4314/bcse.v33i1.15

Highlights

Polyfunctionalized heterocyclic compounds are playing important roles in drug discovery processes and in the analysis of drugs
Pyrroles [1, 2] and their analogues have been receiving attention owing to their biological and pharmacological properties [3] such as human cytomegalovirus (HCMV) protease [4], human cytosolic carbonic anhydrase isozymes [5], they have been used as PI-091 [6], and cardiac cAMPphosphodiestrase [7], many of the alkaloids have pyrrole rings [8]
Due to the above considerations and in continuation of our work on the development of useful and green synthetic methodology for the preparation of biologically active heterocyclic compounds using of caffeine as catalyst [33], we report synthesis of polysubstituted dihydro-2-oxypyrroles via one-pot, four condensation domino reaction between aromatic/ aliphatic amines (1 and 3), dialkyl acetylenedicarboxylate 2 and formaldehyde 4 in the presence

Summary

Introduction

Polyfunctionalized heterocyclic compounds are playing important roles in drug discovery processes and in the analysis of drugs. Due to the above considerations and in continuation of our work on the development of useful and green synthetic methodology for the preparation of biologically active heterocyclic compounds using of caffeine as catalyst [33], we report synthesis of polysubstituted dihydro-2-oxypyrroles via one-pot, four condensation domino reaction between aromatic/ aliphatic amines (1 and 3), dialkyl acetylenedicarboxylate 2 and formaldehyde 4 in the presence

Results

Conclusion