Home / Publications / Recyclization of exo-methylene bielectrophiles with 2-aminobenzimidazoles as an access to 3-substituted pyrimido[1,2-a]benzimidazol-2-ones

Recyclization of exo-methylene bielectrophiles with 2-aminobenzimidazoles as an access to 3-substituted pyrimido[1,2-a]benzimidazol-2-ones

Yuri Alexandrovich Kovygin 1
Yuri Alexandrovich Kovygin
, 
Irina Sergeevna Zotova 1
Irina Sergeevna Zotova
, 
Khidmet Sapharovich Shikhaliev 1
Khidmet Sapharovich Shikhaliev
1 Voronezh State University, 394018 Voronezh, Russian Federation
10.71267/mencom.7892
Published 2026-02-03
Communication , Volume 36, Issue 2, 188-190
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Kovygin Y. A., Zotova I. S., Shikhaliev K. S. Recyclization of exo-methylene bielectrophiles with 2-aminobenzimidazoles as an access to 3-substituted pyrimido[1,2-a]benzimidazol-2-ones // Mendeleev Communications. 2026. Vol. 36. No. 2. pp. 188-190.
GOST all authors (up to 50) Copy
Kovygin Y. A., Zotova I. S., Shikhaliev K. S. Recyclization of exo-methylene bielectrophiles with 2-aminobenzimidazoles as an access to 3-substituted pyrimido[1,2-a]benzimidazol-2-ones // Mendeleev Communications. 2026. Vol. 36. No. 2. pp. 188-190.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.71267/mencom.7892
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7892
TI - Recyclization of exo-methylene bielectrophiles with 2-aminobenzimidazoles as an access to 3-substituted pyrimido[1,2-a]benzimidazol-2-ones
T2 - Mendeleev Communications
AU - Kovygin, Yuri Alexandrovich
AU - Zotova, Irina Sergeevna
AU - Shikhaliev, Khidmet Sapharovich
PY - 2026
DA - 2026/02/03
PB - Mendeleev Communications
SP - 188-190
IS - 2
VL - 36
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2026_Kovygin,
author = {Yuri Alexandrovich Kovygin and Irina Sergeevna Zotova and Khidmet Sapharovich Shikhaliev},
title = {Recyclization of exo-methylene bielectrophiles with 2-aminobenzimidazoles as an access to 3-substituted pyrimido[1,2-a]benzimidazol-2-ones},
journal = {Mendeleev Communications},
year = {2026},
volume = {36},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7892},
number = {2},
pages = {188--190},
doi = {10.71267/mencom.7892}
}
MLA
Cite this
MLA Copy
Kovygin, Yuri Alexandrovich, et al. “Recyclization of exo-methylene bielectrophiles with 2-aminobenzimidazoles as an access to 3-substituted pyrimido[1,2-a]benzimidazol-2-ones.” Mendeleev Communications, vol. 36, no. 2, Feb. 2026, pp. 188-190. https://mendcomm.colab.ws/publications/10.71267/mencom.7892.

Keywords

3,4-dihydropyrimido[1,2-a]benzimidazol-2(1H)-ones
aminobenzimidazoles
aza-Michael addition
bielectrophiles
domino reactions
heterocyclization
itaconimides
methylenebutyrolactone

Abstract

Recyclization of 2-(R-amino)benzimidazoles with N-arylitaconimides affords new 1-R-3,4-dihydropyrimido[1,2-a]-benzimidazol-2(1H)-ones bearing acetanilide moiety at position 3. The similar reaction with α-methylene-γ-butyrolactone gives the analogues containing 2-hydroxyethyl substituent. The domino process starts with the aza-Michael addition of the 3-positioned imine atom of benzimidazoles at the activated exo-methylene group of the bielectrophiles.

Funders

Ministry of Education and Science of the Russian Federation
FRES-2023-0004

References

1.
A Comprehensive Account on Recent Progress in Pharmacological Activities of Benzimidazole Derivatives
Brishty S.R., Hossain M.J., Khandaker M.U., Faruque M.R., Osman H., Rahman S.M.
Frontiers in Pharmacology, 2021
2.
Pyrimido[1,2-a]benzimidazoles: synthesis and perspective of their pharmacological use
Fedotov V.V., Rusinov V.L., Ulomsky E.N., Mukhin E.M., Gorbunov E.B., Chupakhin O.N.
Chemistry of Heterocyclic Compounds, 2021
3.
Utility of Pyrazolylchalcone Synthon to Synthesize Azolopyrimidines under Grindstone Technology
El-Hashash M.A., Gomha S.M., El-Arab E.E.
Chemical and Pharmaceutical Bulletin, 2016
5.
Antiparasitic Activity of Fluorophenyl-Substituted Pyrimido[1,2-a]benzimidazoles
Nasr I.S., Koko W.S., Khan T.A., Schobert R., Biersack B.
Biomedicines, 2023
8.
Pyrimido[1,2-a]benzimidazoles as inhibitors of oncoproteins ubiquitin specific protease 5 and MYCN in the childhood cancer neuroblastoma
Gadde S., Kleynhans A., Holien J.K., Bhadbhade M., Linh Dan Nguyen P., Mittra R., Tin Yu T., Carter D.R., Parker M.W., Marshall G.M., Cheung B.B., Kumar N.
Bioorganic Chemistry, 2023
10.
Discovery of 1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazoles as novel class of corticotropin releasing factor 1 receptor antagonists
Kojima T., Mochizuki M., Takai T., Hoashi Y., Morimoto S., Seto M., Nakamura M., Kobayashi K., Sako Y., Tanaka M., Kanzaki N., Kosugi Y., Yano T., Aso K.
Bioorganic and Medicinal Chemistry, 2018
11.
Intraocular pressure-lowering effects of imidazo[1,2-a]- and pyrimido[1,2-a]benzimidazole compounds in rats with dexamethasone-induced ocular hypertension
Marcus A.J., Iezhitsa I., Agarwal R., Vassiliev P., Spasov A., Zhukovskaya O., Anisimova V., Ismail N.M.
European Journal of Pharmacology, 2019
14.
Palladium-Catalyzed Carbonylative Synthesis of Functionalized Benzimidazopyrimidinones
Gabriele B., Veltri L., Mancuso R., Russo P., Grasso G., Cuocci C., Romeo R.
Synthesis, 2017
15.
A convenient synthesis of new heterocycles from benzimidazoles and carbon suboxide
Bonsignore L., Loy G., Secci D.
Journal of Heterocyclic Chemistry, 1992
18.
Photochemical synthesis of pyrimido[1,2-a]benzimidazole derivatives
Frolov A.N.
Russian Journal of General Chemistry, 2004
20.
Three-component synthesis of 4-aryl-1H-pyrimido[1,2-a]benzimidazole derivatives in ionic liquid
Yao C., Lei S., Wang C., Li T., Yu C., Wang X., Tu S.
Journal of Heterocyclic Chemistry, 2009
21.
TiO2/porous carbon as a new nanocomposite and catalyst for the preparation of 4H-pyrimido[2,1-b]benzimidazoles
Jalilian Z., Moosavi-Zare A.R., Ghadermazi M., Goudarziafshar H.
RSC Advances, 2023
22.
Nucleophilic Substitution of Azide Acting as a Pseudo Leaving Group: One-Step Synthesis of Various Aza Heterocycles
Doebelin C., Schmitt M., Antheaume C., Bourguignon J., Bihel F.
Journal of Organic Chemistry, 2013
23.
Microwave-Assisted Copper Powder-Catalyzed Synthesis of Azole-Fused Pyrimidinones
Quang Dao P.D., Cho C.S., Ho S.L., Sohn H.
Current Organic Chemistry, 2018
24.
A rapid and efficient method for synthesis of pyrimido[1,2-a]-benzimidazole derivatives under microwave irradiation
Zhuang Q., Li C., Tu S., Cao L., Zhou D., Shao Q., Guo C.
Journal of Heterocyclic Chemistry, 2008
25.
ref-10.71267-mendc7412-1-25-1-0
O. V. Burukhina, T. V. Anis'kova and A. Yu. Yegorova
Sovremennye Naukoemkie Tekhnologii, 2012
26.
Synthesis of 3,4-dihydropyrimido[1,2-a]benzimidazoles, promising CRF1 receptor antagonists
Vandyshev D.Y., Kovygin Y.A., Khmelevskaya T.N., Sherbakov K.A., Shikhalieva K.D., Smoliannikova M.Y., Shikhaliev K.S.
Russian Chemical Bulletin, 2024
27.
Rational Design of Multitarget-Directed Ligands: Strategies and Emerging Paradigms.
Zhou J., Jiang X., He S., Jiang H., Feng F., Liu W., Qu W., Sun H.
Journal of Medicinal Chemistry, 2019
28.
Efficient synthesis of (5-oxo-6,7-dihydro-4H-[1,2,4]triazolo-[1,5-a]pyrimidin-6-yl)acetanilides based on the recyclization of N-arylitaconimides with 3-amino[1,2,4]triazoles
Kovygin Y.A., Vandyshev D.Y., Ledenyova I.V., Kosheleva E.A., Polikarchuk V.A., Kozaderov O.A., Shikhaliev K.S.
Russian Chemical Bulletin, 2021
29.
Recyclization of N-arylitaconimides with carboximidamides – a novel efficient method for the synthesis of 2-(2-amino-6-oxo- 1,4,5,6-tetrahydropyrimidin-5-yl)acetanilides
Sotnikov N.M., Kovygin Y.А., Vandyshev D.Y., Ledenyova I.V., Kosheleva Y.А., Kozadyorov O.А., Shikhaliev K.S.
Chemistry of Heterocyclic Compounds, 2021
30.
Kovygin Y.A., Zotova I.S., Sotnikov N.M., Polikarchuk V.A., Shikhaliev K.S.
Mendeleev Communications, 2024