The Pudovik reaction: the synthesis of bioactive α-aminophosphonates with long alkyl chains

Abstract

In this research we investigated the reactions of substituted naphthaldehyde with amines. The condensation of do-, tetra-, hexa-, octadecan-1-amines with 2-hydroxy-1-naphthaldehyde yielded a series of azomethines in good yields. Subsequent reaction of these compounds with didodecylphosphine oxide yielded α-aminophosphonates. The in vitro microbiological activity of the synthesized phosphorus compounds against gram-positive, gram-negative bacteria and the yeast Candida albicans was determined in comparison to standard agents. The synthesized compounds showed a high antibacterial and antimycotic activity against human and animal pathogenic microflora. Every newly synthesized compound was characterized by elemental analyses, IR, ¹H NMR, ³¹P NMR spectral studies. The thermal stability was studied by synchronous thermogravimetry and differential scanning calorimetry (TG/DSC).

Graphical Abstract

Keywords:

• α-aminophosphonates
• long alkyl chains
• antimicrobial activity

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was funded by the subsidy allocated to Kazan Federal University for the state assignment in the sphere of scientific activities (No. 4.5888.2017/8.9).