Abstract
The synthesis of a new class of lawsone enaminone derivatives by using lawsone, triethyl orthoformate and aromatic amines in the presence of guanidinium chloride under solvent-free conditions has been developed.
Highlights
Enaminone derivatives are versatile readily obtainable reagents and their chemistry has received considerable attention in recent years. They have demonstrated a potential as multipurpose synthetic intermediates in organic synthesis such as various heterocyclic compounds,[1,2,3,4,5] synthons for the synthesis of various biologically active compounds such as antitumor, anti-epileptic, anti-in ammatory, antibacterial, anticonvulsant, and other therapeutic agents6–13and a substructure that frequently occurs in natural products.[14]
Considering the above points, and in continuation of our interest on the synthesis of different kinds of heterocyclic compounds based on MCRs,[28] we wish to report one-pot three-component synthesis of new lawsone enaminones from lawsone, triethyl orthoformate and aromatic amines in the presence of guanidinium chloride under solvent-free conditions and investigation of their Z/E(C]C)-isomerization in DMSO-d6 at room temperature by 1H-NMR spectroscopy
We performed the same reaction under solvent-free conditions at 70, 80, 90 C, and observed that the reaction took place smoothly at 90 C, affording the desired product 4a in 85% yield at 15 min (Table 1, entry 7)
Summary
Enaminone derivatives are versatile readily obtainable reagents and their chemistry has received considerable attention in recent years. It has been used as the starting material for the synthesis of a variety of biologically active compounds and materials with interesting properties.[22,23,24,25] In recent decades, it has been used in many reactions for the Catalyst Entry Solvent (mol%) Considering the above points, and in continuation of our interest on the synthesis of different kinds of heterocyclic compounds based on MCRs,[28] we wish to report one-pot three-component synthesis of new lawsone enaminones from lawsone, triethyl orthoformate and aromatic amines in the presence of guanidinium chloride under solvent-free conditions and investigation of their Z/E(C]C)-isomerization in DMSO-d6 at room temperature by 1H-NMR spectroscopy.
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