<i>β</i>-Cyclodextrin Catalyzed, One-Pot Multicomponent Synthesis and Antimicrobial Potential of N-Aminopolyhydroquinoline Derivatives

Abstract

In the present report, we have described the synthesis of N-aminopolyhydroquinoline (N-PHQ) derivatives using highly efficient β-cyclodextrin (β-CD) as a catalyst by the Hantzsch condensation of substituted aromatic aldehydes, dimedone, and hydrazine hydrate in one pot. The reactions were completed in a shorter time without the generation of any other byproduct. The synthesized N-PHQs were washed thoroughly with distilled water and recrystallized with ethanol to get highly purified products (as crystals). The structure of the synthesized N-PHQs was established by using advanced spectroscopic techniques like FT-IR, NMR (1H, 13C, DEPT, COSY, and HSQC), ESI-MS, and Elemental Analyzer. The N-PHQs derivatives demonstrated moderate to excellent resistance against the tested strains (both fungal as well as bacterial). The presence of polar groups, which are able to form H-bonds, attached to the phenyl ring like -NO2 (4b and 4c), and -OMe (4i, 4j, and 4k) exhibits excellent activity, which is comparable to standard drugs, amoxicillin and fluconazole.

Keywords

• polyhydroquinoline
• <i>β</i>-cyclodextrin
• catalyst
• Hantzsch reaction
• antimicrobial activity