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

• features a broad substrate scope, simple reaction conditions, and high molecular convergence. Keywords: acylhydrazone; annulation; azepine; MBH carbonate; spirooxindole; Introduction Among the various N-containing heterocyclic compounds, 1,2-diazepine represents one of the important privileged structural

• equivalent, the yield of spiro compound 3a decreased to 35% (Table 1, entry 17). At last, if the amount of α-halogenated acylhydrazone was reduced, the yield of product 3a also decreased to 57% yield (Table 1, entry 18). Thus, the best reaction conditions were carrying out the reaction in DCM at room

• [indoline-3,5'-[1,2]diazepines] 3a–l: A 10 mL reaction tube was charged with α-halogenated acylhydrazone (0.2 mmol), MBH nitrile of isatin (0.1 mmol), triethylamine (0.2 mmol) and dichloromethane (4.0 mL) and the mixture was stirred at room temperature for 24 hours. After removing the solvent by rotatory

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

• an extension of their trifluoromethyl acylhydrazone synthesis, Hu et al. reported that trifluoromethyl acylhydrazones react with azomethine ylides [118] and ethyl isocyanoacetate [119] to generate trifluoromethylated imidazolidines. They demonstrated then that trifluoromethyl acylhydrazones act as

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

• proved the promising anti-PD and metallophoric effect, especially towards intracellularly relevant copper(I) ions, of X1INH (1-methyl-1H-imidazole-2-carboxaldehyde isonicotinoyl hydrazone) [32]. This year, we evaluated the effects of the presence of three methoxy substituents in an N-acylhydrazone

• stronger character of the intramolecular H-bond in the nitro-substituted N-acylhydrazone. As previously observed for other compounds of this class, the azomethine ν(C=N) modes are barely susceptible to interactions involving the nitrogen atom, being located at 1620 cm−1 in hdz-CH3 and at 1622 cm−1 in

Menadione: a platform and a target to valuable compounds synthesis

• Acácio S. de Souza,
• Ruan Carlos B. Ribeiro,
• Dora C. S. Costa,
• Fernanda P. Pauli,
• David R. Pinho,
• Matheus G. de Moraes,
• Fernando de C. da Silva,
• Luana da S. M. Forezi and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

• ]. Examining a broad range of hydrazides in the condensation reaction with menadione, Bouhadir and co-workers reported the synthesis of various menadione acylhydrazone derivatives [126]. In this work, various acylhydrazides prepared by reaction of hydrazine hydrate with different esters were reacted with

One-pot activation–alkynylation–cyclization synthesis of 1,5-diacyl-5-hydroxypyrazolines in a consecutive three-component fashion

• Christina Görgen,
• Katharina Boden,
• Guido J. Reiss,
• Walter Frank and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2019, 15, 1360–1370, doi:10.3762/bjoc.15.136

• ] specifically have been published employing a cyclizing addition of an acylhydrazone to the carbonyl group as a ring-forming reaction [32][33][34][35][36][37][38][39][40], their diversity-oriented one-pot synthesis in a multicomponent approach has remained unexplored to date. In the course of our program