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
| Autor: | Reena Chib, Inshad Ali Khan, Rashmi Sharma, Parteek Kour, Anil Kumar, Vijai K. Rai |
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| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry General Chemistry 010402 general chemistry 01 natural sciences Aldehyde 0104 chemical sciences chemistry.chemical_compound chemistry Salicylaldehyde Phosphite ester Yield (chemistry) Michael reaction Organic chemistry Knoevenagel condensation Triethylamine Malononitrile |
| Zdroj: | Research on Chemical Intermediates. 43:7319-7329 |
| ISSN: | 1568-5675 0922-6168 |
| DOI: | 10.1007/s11164-017-3077-2 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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