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

• Chemistry Department, RUDN University, 6 Miklukho-Maklaya St., 117198 Moscow, Russian Federation 10.3762/bjoc.20.236 Abstract The heterocyclic core of imidazo[1,2-a]pyrimidine was formed in satisfactory yields as a result of the interaction of the readily available 2-aminoimidazole with N-substituted

• 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

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

• Cristina Martini,
• Muhammad Idham Darussalam Mardjan and
• Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

• use of triflic acid (TfOH) resulted also in the cleavage of the alkyl group derived from the isocyanide, with formation of 47 (Scheme 18). Kanizsai et al. [51] have reported the synthesis of 4,5-disubstituted 2-amino-1H-imidazoles and their further modification through the GBB-3CR. The 2

• -aminoimidazole moiety can be found in different alkaloids isolated from sponges and exhibits useful bioactive properties. The methodology employed by the authors to assemble C4/C5-functionalized 2-aminoimidazoles 49 exploited a Mannich condensation followed by an iodoxybenzoic acid (IBX) and N-iodophthalimide

• diversification points. The scope of the reaction was limited: alkyl aldehydes and aryl/benzyl isocyanides could not be used, and 4 distinct compounds were obtained in yields of 23–40%. Nevertheless, these results represent an improvement compared to previous studies where substitution on C4 of the 2

Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds

• Victoria V. Lipson,
• Tetiana L. Pavlovska,
• Nataliya V. Svetlichnaya,
• Anna A. Poryvai,
• Nikolay Yu. Gorobets,
• Erik V. Van der Eycken,
• Irina S. Konovalova,
• Svetlana V. Shiskina,
• Alexander V. Borisov,
• Vladimir I. Musatov and
• Alexander V. Mazepa

Beilstein J. Org. Chem. 2019, 15, 1032–1045, doi:10.3762/bjoc.15.101

• considered as the analogues of both 3,3’-spirooxindole and 2-aminoimidazole marine sponge alkaloids. Keywords: 2-amino-4-arylimidazole; (2-amino-4-arylimidazolyl)propanoic acid; isatin; Meldrum’s acid; multicomponent reactions; pyrrolo[1,2-c]imidazole; 3,3’-spirooxindoles; Introduction Heterocyclic

• derivatives containing pyrrole and 2-aminoimidazole fragments in their structure were found among the metabolites of these marine organisms [1]. This group of compounds is characterized by an exceptional molecular diversity. The main structural types of these substances are shown in Figure 1. The metabolites

• of Leucetta Sp. and Clathrina Sp. are presented by achiral imidazole alkaloids from the group of benzyl substituted 2-aminoimidazole (dorimidazole A (I), naamine A (II)), fused cyclic systems (2-amino-2-deoxykealiiquinone (III)) and spiro-linked compounds ((−)-spirocalcaridine B (IV)) [2]. Agelas Sp

Bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina lacunosa

• Qun Göthel,
• Thanchanok Sirirak and
• Matthias Köck

Beilstein J. Org. Chem. 2015, 11, 2334–2342, doi:10.3762/bjoc.11.254

• 6.66 (d, J = 15.8 Hz, H-8) to δC 134.9 (C-1). 1H,1H-COSY correlations in between 9-NH (δ 8.17)/H-10 (δ 3.20, 2H)/H-11 (δ 1.71, 2H)/H-12 (δ 2.45, 2H) indicated a propanamine fragment which was connected to a 2-aminoimidazole moiety according to 1H,13C-HMBC correlations from H-12 to δC 126.8 (C-13) and