Abstract
A simple and versatile method for the synthesis of 1,5-benzodiazepines is via condensation of o-phenylenediamines (OPDA) and ketones in the presence of catalytic amount of H-MCM-22 using acetonitrile as solvent at room temperature. In all the cases, the reactions are highly selective and are completed within 1–3 h. The method is applicable to both cyclic and acyclic ketones without significant differences. The reaction proceeds efficiently under ambient conditions with good-to-excellent yields.
Highlights
Benzodiazepines constitute an important class of biologically active compounds and their synthesis has been receiving much attention in the field of medicinal and pharmaceutical chemistry owing to their application as anticonvulsant, antiinflammatory, analgesic, hypnotic, and sedative agents and to their hypnotic activity [1–6]
Benzodiazepines are generally synthesized by the condensation of o-phenylenediamine (OPDA) with a,b-unsaturated carbonyl compounds, b-haloketones, or with ketones [12] using acidic catalysts which are critical to enhance the condensation process
Different reagents such as BF3-etherate, polyphosphoric acid, NaBH4, MgO/POCl3, Yb(OTf)[3], Ga(OTf)[3], lead nitrate, L-proline, acetic acid under microwave conditions, molecular iodine, and ionic liquids have been used for the synthesis of benzodiazepines [13–23]
Summary
Benzodiazepines constitute an important class of biologically active compounds and their synthesis has been receiving much attention in the field of medicinal and pharmaceutical chemistry owing to their application as anticonvulsant, antiinflammatory, analgesic, hypnotic, and sedative agents and to their hypnotic activity [1–6]. Benzodiazepines are generally synthesized by the condensation of o-phenylenediamine (OPDA) with a,b-unsaturated carbonyl compounds, b-haloketones, or with ketones [12] using acidic catalysts which are critical to enhance the condensation process. Different reagents such as BF3-etherate, polyphosphoric acid, NaBH4, MgO/POCl3, Yb(OTf)[3], Ga(OTf)[3], lead nitrate, L-proline, acetic acid under microwave conditions, molecular iodine, and ionic liquids have been used for the synthesis of benzodiazepines [13–23]. The solid oxide catalyst used previously had poor textural parameters such as low surface area and pore volume which do not support a better performance in the synthesis of benzodiazepines. The effect of catalyst and the catalyst concentration on the above process has been investigated in detail
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