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

• -derived NH-acylhydrazones to build 1,3,4-oxadiazole derivatives in good yields. The electrolysis was conducted under galvanostatic conditions in methanol using a carbon graphite anode and a platinum cathode. From a mechanistic point of view, in situ condensation of acylhydrazines 28 with α-keto acids 27

Trifluoromethylated hydrazones and acylhydrazones as potent nitrogen-containing fluorinated building blocks

• Zhang Dongxu

Beilstein J. Org. Chem. 2023, 19, 1741–1754, doi:10.3762/bjoc.19.127

• building blocks [91] (Scheme 14). Inspired by previous accounts and this work [92][93], Hu et al. explored 1,2- nucleophilic addition reactions of trifluoromethylated acylhydrazones with organometallic reagents for the synthesis of trifluorinated homoallylic acylhydrazines [94][95][96][97][98

• ], trifluorinated α-methylene-γ-lactams [99][100], and β-trifluoromethyl-β-acylhydrazonyl carbonyl compounds [101] (Scheme 15). Among these fluorinated products, the trifluoromethylated homoallylic acylhydrazines were easily transformed to CF3-substituted pyrazolines and 1,6-dihydropyridazines via a cascade

• acylhydrazines. Synthesis of trifluoromethylated cyanohydrazines and 3-trifluoromethyl-1,2,4-triazolines. N-Arylation and N-alkylation of trifluoromethyl acylhydrazones. [3 + 2]-Cycladditions of trifluoromethyl acylhydrazones.

Consecutive hydrazino-Ugi-azide reactions: synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles

• Angélica de Fátima S. Barreto,
• Veronica Alves dos Santos and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2017, 13, 2596–2602, doi:10.3762/bjoc.13.256

• ) allow the construction of relatively complex molecules through a one-pot synthesis. The combination of IMCRs in a consecutive or sequential fashion further extends the complexity of the molecules obtained. Herein, we report the efficient application of this approach to the synthesis of acylhydrazines

• . The products synthesized herein contain functional groups within their structures that can be easily modified to obtain new acylhydrazino 1,5-disubstituted tetrazoles. Keywords: acylhydrazines; consecutive Ugi reactions; 1,5-disubstituted tetrazoles; isocyanide-based multicomponent reactions (IMCRs

• linatine [24] and the antibiotic negamycin, active against Gram-negative bacteria [25], among others [26]. Furthermore, trisubstituted acylhydrazines were found to serve as tertiary amide bioisosters [27]. Therefore, it is highly desirable to have a method that allows an easy incorporation of hydrazino

Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia

• Artem N. Semakin,
• Aleksandr O. Kokuev,
• Yulia V. Nelyubina,
• Alexey Yu. Sukhorukov,
• Petr A. Zhmurov,
• Sema L. Ioffe and
• Vladimir A. Tartakovsky

Beilstein J. Org. Chem. 2016, 12, 2471–2477, doi:10.3762/bjoc.12.241

• -substituted hydrazones 1 were prepared from the corresponding carbonyl compounds and acylhydrazines or carbazates to study the reaction with amines (Scheme 2, for details see Supporting Information File 1). Acetic acid was added as catalyst and for suppression of the side reaction of the formed α-halogen

• ://www.ccdc.cam.ac.uk/conts/retrieving.html (or from the CCDC, 12 Union Road, Cambridge, CB21EZ, UK; or deposit@ccdc.cam.ac.uk). Proposed approach to the synthesis of I. Synthesis of α-halogen-substituted hydrazones 1 from α-halocarbonyl compounds and acylhydrazines or carbazates. Synthesis of a mixed triazole