Abstract
A simple and efficient method is presented for the synthesis of benzodiazepines through the multicomponent reaction of o-phenylenediamine, various aldehydes and 5,5-dimethylcyclohexane-1,3-dione (dimedone) in the presence of the acidic bis ionic liquid 1,4-diazabicyclo[2.2.2]octanium diacetate under ultrasound irradiation. The ionic liquid used is recoverable and reusable. This procedure is simple and environmentally friendly, and offers easy work-up, mild conditions and excellent yield in a short reaction time. All of the synthesized compounds were characterized by IR, 1H NMR, mass spectrometry and elemental analysis.
Highlights
Benzodiazepines are generally synthesized by the reaction of β-haloketones with o-phenylenediamine,13 condensation of α,β-unsaturated compounds with o-phenylenediamines14 and condensation of ketones with o-phenylenediamine in the presence of ytterbium trichloride
Multicomponent reactions (MCRs) combined with ionic liquid can assist in the synthesis of the benzodiazepines to reduce the cost of starting materials and decrease the generation of undesirable by-products
We were interested in the synthesis of benzodiazepines under ultrasound irradiation at various temperatures
Summary
Benzodiazepine rings are important building blocks of heterocyclic and pharmaceutical compounds because they are anti-inflammatory, antidepressive, anticonvulsant, antiviral, antimicrobial, anti-HIV, antianxiety, anti-ulcerative, antitumor, analgesic, antihistaminic, anti-allergic, hypnotic and antipyretic. Some benzodiazepines are used in industry as dyes. Others are useful precursors for the synthesis of fused-ring compounds such as oxazino-, triazolo-, tetrazolo-, oxadiazolo- and furanobenzodiazepines.. Benzodiazepines are generally synthesized by the reaction of β-haloketones with o-phenylenediamine, condensation of α,β-unsaturated compounds with o-phenylenediamines and condensation of ketones with o-phenylenediamine in the presence of ytterbium trichloride.. The disadvantages of previously reported procedures for the synthesis of benzodiazepines are their multistep reactions, anhydrous conditions, tedious work-up, long reaction times and generation of undesirable by-products.. Multicomponent reactions (MCRs) are efficient tools in modern synthetic organic chemistry because they are fast, simple, offer high-atomic efficiency, are environmentally friendly and save time and energy.. MCRs combined with ionic liquid can assist in the synthesis of the benzodiazepines to reduce the cost of starting materials and decrease the generation of undesirable by-products. In continuation of our studies on the green synthesis of organic materials, some derivatives of benzodiazepine were synthesized using the ionic liquid 1,4-diazabicyclo[2.2.2]octaniumdiacetate (DABCO-diacetate) under ultrasound irradiation in an MCR
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