Synthesis and antimycotic activity of new derivatives of imidazo[1,2-a]pyrimidines

• Dmitriy Yu. Vandyshev,
• Daria A. Mangusheva,
• Khidmet S. Shikhaliev,
• Kirill A. Scherbakov,
• Oleg N. Burov,
• Alexander D. Zagrebaev,
• Tatiana N. Khmelevskaya,
• Alexey S. Trenin and
• Fedor I. Zubkov

Beilstein J. Org. Chem. 2024, 20, 2806–2817, doi:10.3762/bjoc.20.236

• maleimides or N-arylitaconimides. The mechanism of the studied processes was postulated basing on experimental data, HPLC–MS analysis of reaction mixtures, and quantum chemical calculations. Molecular docking results of the obtained imidazo[1,2-a]pyrimidines, when compared with voriconazole, a drug already

• in clinical use, suggest that they may possess antifungal activity against Candida albicans. Keywords: 2-aminoimidazole; antimycotic activity; imidazo[1,2-a]pyrimidine; molecular docking; N-arylitaconimides; N-substituted maleimides; recyclization; Introduction Nitrogen-containing heterocyclic

• ]pyrimidines using readily available derivatives of azaheterocycles as starting materials. As the last ones, we chose the reaction between 2-aminoimidazole and N-arylitaconimides or N-substituted maleimides, which can be analyzed by both classical synthetic and quantum DFT methods. The second problem solved in

A novel synthetic approach to hydroimidazo[1,5-b]pyridazines by the recyclization of itaconimides and HPLC–HRMS monitoring of the reaction pathway

• Dmitry Yu. Vandyshev,
• Khidmet S. Shikhaliev,
• Andrey Yu. Potapov,
• Michael Yu. Krysin,
• Fedor I. Zubkov and
• Lyudmila V. Sapronova

Beilstein J. Org. Chem. 2017, 13, 2561–2568, doi:10.3762/bjoc.13.252

• the exocyclic activated C=C double bond allows itaconimides to react with heteroaromatic dinucleophiles as dielectrophilic reagents with the possibility of recyclization. Recently, our group reported the first example of this recyclization with N-arylitaconimides 1 and 1,2-diaminobenzimidazole (2) as

• 1,3-N,N-dinucleophile, leading to tetrahydropyrimido[1,2-a]benzimidazoles 3 (Scheme 4) [38]. In continuation of our studies on the synthesis of azolo-annelated heterocycles we herein report the results of our investigations on the reactions between N-arylitaconimides and 1,2-diamino-4-phenylimidazole

• as a heterocyclic C,N/N,N polynucleophile. Results and Discussion Our earlier studies and literature information have shown that acetic acid significantly accelerates the reactions of 1,2-diaminoimidazole with 1,3-dielectrophilic reagents. Therefore, the heterocyclization of N-arylitaconimides 1a–g

Conjugate addition–enantioselective protonation reactions

• James P. Phelan and
• Jonathan A. Ellman

Beilstein J. Org. Chem. 2016, 12, 1203–1228, doi:10.3762/bjoc.12.116

• thiourea catalyst 92 in high yield and modest enantioselectivity (Scheme 22) [45]. Tan and co-workers have investigated the conjugate addition–enantioselective protonation of N-arylitaconimides 95 using a C2-symmetric guanidine catalyst (Scheme 23) [24][46]. Because E- and Z-enolates can exhibit different

• thiols to N-arylitaconimides. Enantioselective addition of thiols to α-substituted N-acryloylamides. Kobayashi’s enantioselective addition of thiols to α,β-unsaturated ketones. Feng’s enantioselective addition of pyrazoles to α-substituted vinyl ketones. Luo and Cheng’s addition of indoles to vinyl