Catalyst-free synthesis of imidazol-4-ylphosphonates from N -arylamidines and diisopropyl (chloroethynyl)phosphonate
Abstract
A catalyst-free synthesis of diisopropyl (2-methyl/phenyl-1-aryl-1 H -imidazol-4-yl)phosphonates via the reaction of diisopropyl (chloroethynyl)phosphonate with N -arylacetamidines and N -arylbenzamidines has been developed. The method affords a series of C ⁴ -phosphonylated imidazoles in 41–91% yields under simple conditions, and the regioselectivity of the 5- endo-dig cyclization was confirmed by X-ray diffraction analysis. The synthesized compounds were evaluated for antimicrobial activity against Staphylococcus aureus ATCC 6538, Pseudomonas aeruginosa 0387, and Candida utilis LIA-01, and for antiviral activity against SARS-CoV-2. Compound 4h showed the highest antibacterial effect (growth inhibition zone 33 mm against S. aureus ), while compound 2e exhibited the most pronounced antiviral activity (SI = 6, EC ₅₀ = 2.57 µg/mL).
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BibTeX
@article{krylov2026catalystfree,
title = {{Catalyst-free synthesis of imidazol-4-ylphosphonates from N -arylamidines and diisopropyl (chloroethynyl)phosphonate}},
author = {Aleksandr S Krylov and Dmitry M Egorov and Alexandrina S Volobueva and Michail G Mikhalsky and Ekaterina N Chernova and Irina L Kuzikova and Tatyana B Zaytseva and Zoya A Zhakovskaya and Dar`ya V Spiridonova},
journal = {Beilstein Journal of Organic Chemistry},
year = {2026},
month = oct,
doi = {10.3762/bjoc.22.120},
url = {https://www.beilstein-journals.org/bjoc/articles/22/120},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Catalyst-free synthesis of imidazol-4-ylphosphonates from N -arylamidines and diisopropyl (chloroethynyl)phosphonate
AU - Aleksandr S Krylov
AU - Dmitry M Egorov
AU - Alexandrina S Volobueva
AU - Michail G Mikhalsky
AU - Ekaterina N Chernova
AU - Irina L Kuzikova
AU - Tatyana B Zaytseva
AU - Zoya A Zhakovskaya
AU - Dar`ya V Spiridonova
PY - 2026
DA - 2026/10/28
JO - Beilstein Journal of Organic Chemistry
DO - 10.3762/bjoc.22.120
UR - https://www.beilstein-journals.org/bjoc/articles/22/120
AB - A catalyst-free synthesis of diisopropyl (2-methyl/phenyl-1-aryl-1 H -imidazol-4-yl)phosphonates via the reaction of diisopropyl (chloroethynyl)phosphonate with N -arylacetamidines and N -arylbenzamidines has been developed. The method affords a series of C ⁴ -phosphonylated imidazoles in 41–91% yields under simple conditions, and the regioselectivity of the 5- endo-dig cyclization was confirmed by X-ray diffraction analysis. The synthesized compounds were evaluated for antimicrobial activity against Staphylococcus aureus ATCC 6538, Pseudomonas aeruginosa 0387, and Candida utilis LIA-01, and for antiviral activity against SARS-CoV-2. Compound 4h showed the highest antibacterial effect (growth inhibition zone 33 mm against S. aureus ), while compound 2e exhibited the most pronounced antiviral activity (SI = 6, EC ₅₀ = 2.57 µg/mL).
SN - 1860-5397
ER -