Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold

• Thierry Milcent,
• Pascal Retailleau,
• Benoit Crousse and
• Sandrine Ongeri

Beilstein J. Org. Chem. 2024, 20, 3174–3181, doi:10.3762/bjoc.20.262

• could easily be synthesized under the same reaction conditions starting from the corresponding hydrazide amino acid. Compounds 3e and 3f were obtained as a mixture of conformers (1:1 ratio) which is often observed with N-acylhydrazones [29][30][31]. Indeed, in theory, N-acylhydrazones can exhibit four

Harnessing the versatility of hydrazones through electrosynthetic oxidative transformations

• Aurélie Claraz

Beilstein J. Org. Chem. 2024, 20, 1988–2004, doi:10.3762/bjoc.20.175

• synthesis of pyrazolo[4,3-c]quinoline derivatives 22 from 7-chloro-4-hydrazinoquinolines 20 and aromatic aldehydes 21 (Scheme 5) [40]. In 1992, Chiba and Okimoto reported the electrooxidative cyclization of aldehyde and ketone-derived N-acylhydrazones 23a and 23b to build 1,3,4-oxadiazoles 24a and Δ3-l,3,4

Construction of diazepine-containing spiroindolines via annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates

• Xing Liu,
• Wenjing Shi,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 1923–1932, doi:10.3762/bjoc.19.143

• and proceeds through a by base-promoted annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates. The reaction mechanism of this formal [4 + 3] annulation includes the in situ generated allylic ylide, nucleophilic substitution, Michael additon, and elimination processes

• -derived MBH carbonates with α-halogenated N-acylhydrazones for the convenient synthesis of functionalized spiro[indoline-3,5'-[1,2]diazepine] derivatives (reaction 5 in Scheme 1). Results and Discussion Initially, the reaction conditions were screened by employing α-chloro-N-benzoylhydrazone 1a and MBH

• [indoline-3,5'-[1,2]diazepines] 3a–m were obtained in reasonable to good yields. Both, α-chloro- and α-bromo-N-acylhydrazones could be successfully used in the reaction and gave similar results. Also, hydrazones with different benzoyl-protecting groups were well tolerated in the reaction. In general, α

Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups

• Dayanne Martins,
• Roberta Lamosa,
• Talis Uelisson da Silva,
• Carolina B. P. Ligiero,
• Sérgio de Paula Machado,
• Daphne S. Cukierman and
• Nicolás A. Rey

Beilstein J. Org. Chem. 2023, 19, 1713–1727, doi:10.3762/bjoc.19.125

• Inorgânica, Universidade do Estado do Rio de Janeiro (UERJ), Rio de Janeiro, 20950-000, Brazil 10.3762/bjoc.19.125 Abstract N-Acylhydrazones are a versatile class of organic compounds with a diversity of potential applications. In this study, two new structure-related 3,4,5-trimethoxybenzoyl-containing N

• compounds are stable at physiological-like conditions, especially the methyl-derived one, which qualifies them for further toxicological and activity studies, such as those involving trivalent metal ions sequestering in the context of neurodegenerative diseases. Keywords: DFT calculations; N-acylhydrazones

• ; phenol acidity; ring substituents; XRD; Introduction N-Acylhydrazones are a class of compounds that contain the hydrazonic functional group (–NH–N=C–) attached to an acyl group, which can be modified to generate a range of different structures with varying properties [1]. The versatility of this class