Facile synthesis of hydantoin/1,2,4-oxadiazoline spiro-compounds via 1,3-dipolar cycloaddition of nitrile oxides to 5-iminohydantoins

• Juliana V. Petrova,
• Varvara T. Tkachenko,
• Victor A. Tafeenko,
• Anna S. Pestretsova,
• Vadim S. Pokrovsky,
• Maxim E. Kukushkin and
• Elena K. Beloglazkina

Beilstein J. Org. Chem. 2025, 21, 1552–1560, doi:10.3762/bjoc.21.118

• shown to exceed previously known spiro-compounds bearing only hydantoins or 1,2,4-oxadiazolines (IC50 values were 30–50 μM, HCT116 cell lines). Keywords: 1,3-dipolar cycloaddition; hydantoins; nitrile oxides; Shiff bases; spiro-compounds; Introduction The 1,2,4-oxadiazole fragment is a common

New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized

• Maryna V. Murlykina,
• Maryna N. Kornet,
• Sergey M. Desenko,
• Svetlana V. Shishkina,
• Oleg V. Shishkin,
• Aleksander A. Brazhko,
• Vladimir I. Musatov,
• Erik V. Van der Eycken and
• Valentin A. Chebanov

Beilstein J. Org. Chem. 2017, 13, 1050–1063, doi:10.3762/bjoc.13.104

• basic. DMF increases solubility of imines 5, while the application of strong acid (HClO4) promotes Shiff bases protonation. Phenylpyruvic acid (1') was also applied as carbonyl component in GBB-3CR to obtain imidazopyrazoles having a carboxylic group. However, the process of decarboxylation took place

A novel family of (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids – analogues of α-amino acids

• Natalia V. Pavlenko,
• Tatiana I. Oos,
• Yurii L. Yagupolskii,
• Igor I. Gerus,
• Uwe Doeller and
• Lothar Willms

Beilstein J. Org. Chem. 2014, 10, 722–731, doi:10.3762/bjoc.10.66

• ; hydrophosphinylation; organo-fluorine; Shiff bases; (trifluoromethyl)phosphinic acid; Introduction For a long time aminophosphonic and aminophosphinic acids as isosters of aminocarboxylic acids have attracted a particular interest for the preparation of analogues of numerous natural products. Among the literature

• reactions with Shiff bases to give adducts 17 in satisfactory yields and these were successfully transformed into the appropriate free acids 14. The same series of Shiff bases was used to explore the reactivity of ethyl (difluoromethyl)phosphinate (5) in reactions with C=N double bonds and the desired (α

• removed during the reaction due to the high acidity of the CF3 phosphinic acid group. The variability of Schiff bases ensures access to a range of structurally diverse phosphinic acid analogues of amino acids in the relatively simple way. Thus, we investigated the hydrophosphinylation of some Shiff bases