Zirconium(IV) chloride-catalyzed synthesis of 1,5-benzodiazepine derivatives

Abstract

Zirconium tetrachloride efficiently catalyzes the cyclocondensation reaction of o-phenylenediamine and a ketone in refluxing 1,2-dichloroethane to afford the corresponding 2,3-dihydro-1H-1,5-benzodiazepine in high yield. The formation of specific regioisomers and their structural elucidation are reported for the first time.Key words: zirconium tetrachloride, o-phenylenediamines, ketones, 1,5-benzodiazepines, 1H NMR, regioisomers.

Synthesis, characterization, and catalytic activity of a polymer-supported copper(II) complex with a thiosemicarbazone ligand

“…This suggests that the ligand chelates through its N (azomethine) and S atoms. In complex 5, [Cu-TSC], bands at 412, 320 and 306 cm -1 were assigned to m(Cu-N) [27], m(Cu-S) [28], and m(Cu-Cl) [29], respectively. The FTIR spectra of the polymer-supported Schiff base ligand and polymer-supported complex were also studied.…”

Facile Synthesis of Perfluoroalkyl Substituted 1H-Benzo[b][1,4]-diazepine-2(3H)-ones via a Catalyst-Free Process

“…在以往文献报道 [3,8,9] 和我们自己工作的基础上, 推 断反应机理如 Scheme 1. [8] 138.3, 136.8, 134.9, 134.6, 133.4, 133.1, 131.6, 130.6, 130.5, 129.4, 128.5, 123.4, 120.3 (q, 1 J C -F ＝275 Hz), 38.…”

Applications of Zirconium (IV) Compounds in Organic Synthesis

“…The classical method for the preparation of 1,5-benzodiazepine derivatives is a one-pot condensation of ophenylenediamines with , -unsaturated carbonyl compounds, -haloketones, or ketones [93]. Reddy and coworkers reported that ZrCl 4 is an efficient catalyst for the synthesis of 1,5-benzodiazepine derivatives by cyclocondensation of ketones with o-phenylenediamines [94].…”