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Synthesis of 2-amino-4H-chromen-4-ylphosphonates and β-phosphonomalonates via tandem Knoevenagel–Phospha-Michael reaction and antimicrobial evaluation of newly synthesized β-phosphonomalonates

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Abstract

In this manuscript we have demonstrated a new approach for the synthesis of 2-amino-4H-chromen-4-ylphosphonates and β-phosphonomalonates linked 2-chloroquinoline-3-carbaldehyde by modified one-pot three-component tandem Knoevenagel–Phospha-Michael reaction of salicylaldehyde/aryl aldehyde/2-chloroquinoline-3-carbaldehyde, malononitrile/ethylcyanoacetate, and phosphite ester using triethylamine (1–10 mol%) in ethanol under reflux conditions. The desired products were obtained in 86–97% yield in 8–35 h. The advantages of this protocol are its operational simplicity, low catalytic loading, no side product formation, and high yield of product. The newly synthesized β-phosphonomalonates, diethyl-(2-chloroquinolin-3-yl)-2,2-dicyanoethyl)-phosphonates (4a–i) have been tested on two fungal strains (C. albicans and A. fumigatus) and two bacterial strains (S. aureus and E. coli) and their minimum inhibitory concentration was also determined by microbroth dilution method.

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Acknowledgements

We are thankful to SAIF Chandigarh for providing spectral data. P. K. thanks to UGC, Govt. of India for BSR fellowship.

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Authors and Affiliations

  1. Synthetic Organic Chemistry Laboratory, Faculty of Sciences, Shri Mata Vaishno Devi University, Katra, Jammu and Kashmir, 182 320, India

    Parteek Kour & Anil Kumar

  2. Clinical Microbiology Division, Indian Institute of Integrative Medicine, Canal Road, Jammu, 180001, India

    Rashmi Sharma, Reena Chib & Inshad Ali Khan

  3. Department of Chemistry, Guru Ghasidas Vishwavidyalaya, Bilaspur, Chhattisgarh, 495009, India

    Vijai K. Rai

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  1. Parteek Kour
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Correspondence to Anil Kumar.

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Kour, P., Kumar, A., Sharma, R. et al. Synthesis of 2-amino-4H-chromen-4-ylphosphonates and β-phosphonomalonates via tandem Knoevenagel–Phospha-Michael reaction and antimicrobial evaluation of newly synthesized β-phosphonomalonates. Res Chem Intermed 43, 7319–7329 (2017). https://doi.org/10.1007/s11164-017-3077-2

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