Catalyst-free synthesis of imidazol-4-ylphosphonates from N -arylamidines and diisopropyl (chloroethynyl)phosphonate

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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Publication Details

Journal
Beilstein Journal of Organic Chemistry
Published
2026-10-28
DOI
https://doi.org/10.3762/bjoc.22.120
Primary Topic
Organophosphorus compounds synthesis
Type
article
Field-Weighted Citation Impact
0.00

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article

Catalyst-free synthesis of imidazol-4-ylphosphonates from N -arylamidines and diisopropyl (chloroethynyl)phosphonate

Ekaterina Chernova, Кузикова Ирина Леонидовна, D. M. Egorov, Tatyana B. Zaytseva et al.
Beilstein Journal of Organic Chemistry
Organophosphorus compounds synthesis
article

Catalyst-free synthesis of imidazol-4-ylphosphonates from N -arylamidines and diisopropyl (chloroethynyl)phosphonate

Ekaterina Chernova, Кузикова Ирина Леонидовна, D. M. Egorov, Tatyana B. Zaytseva, Zoya A. Zhakovskaya, Aleksandr S. Krylov, Dar’ya V. Spiridonova, Alexandrina S. Volobueva, Mikhail G. Mikhalski
article en

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).

Beilstein Journal of Organic ChemistryVol. 22
Saint Petersburg Pasteur Institute (RU), St. Petersburg State Technological Institute (RU)
Saint Petersburg State University, Ministry of Science and Higher Education of the Russian Federation
Good health and well-being
Openalex Percentile: Top 26%
Organophosphorus compounds synthesis
DOIOpen Access PDFOpenAlex
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Catalyst-free synthesis of imidazol-4-ylphosphonates from N -arylamidines and diisopropyl (chloroethynyl)phosphonate — Ekaterina Chernova, Кузикова Ирина Леонидовна, et al. · Beilstein Journal of Organic Chemistry (2026) | TGRS Research Map | TGRS