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

• spectroscopy, HPLC–HRESIMS) of the products of the investigated reactions unambiguously confirms the processes proceeding along routes A1 and B1 with the formation of N-aryl(alkyl)-7-oxo-5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidin-5-carboxamides 4a–i and N-aryl-2-(7-oxo-5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidin

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

• -addition by the activated C=C double bond and subsequent intramolecular recyclization of the intermediate with the amino group involved. Keywords: cascade reaction; diaminoimidazoles; HPLC–HRESIMS; imidazo[1,5-b]pyridazines; itaconimides; Introduction Among the numerous bicyclic fused imidazole

• the HPLC–HRESIMS monitoring of the reaction confirm its selectivity. Conclusion In summary, a new regioselective and chemoselective cascade reaction of N-arylitaconimides with 1,2-diamino-4-phenylimidazole as 1,3-C,N-dinucleophile was developed to synthesize tetrahydroimidazo[1,5-b]pyridazines. The

• of the interaction of itaconimides 1 with diaminoimidazole 4. 1H,13C-HMBC correlations: the most significant correlations for imidazopyridazine 9d and possible for imidazodiazepine 10d. Yields of the interaction products 9 of N-arylitaconimides 1a–g and diaminoimidazole 4. Results of HPLC–HRESIMS