Green technologies in organic synthesis: self-condensation of enamines, enaminones and enaminoesters under microwave irradiation in ionic liquid

Al‐Zaydi, Khadijah M.; Nhari, Laila M.; Borik, Rita M.; Elnagdi, Mohamed H.

doi:10.1080/17518250903567261

Cited by 24 publications

(10 citation statements)

References 21 publications

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“…Microwave irradiation can also employed be in the synthesis of enaminones [ 11 ]. The enaminone 1,3,5- tris (3-dimethylamino-1-oxoprop-2-en-yl)benzene 1 was synthesized according to a synthetic methodology adapted from the literature [ 11 , 12 , 13 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Crystal Structure, and Supramolecular Understanding of 1,3,5-Tris(1-phenyl-1H-pyrazol-5-yl)benzenes

et al. 2017

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Understanding the supramolecular environment of crystal structures is necessary to facilitate designing molecules with desirable properties. A series of 12 novel 1,3,5-tris(1-phenyl-1H-pyrazol-5-yl)benzenes was used to assess the existence of planar stacking columns in supramolecular structures of pyrazoles. This class of molecules with different substituents may assist in understanding how small structural changes affect the supramolecular environment. The obtained compounds did not present the formation of planar stacking interactions between benzenes in solid or liquid states. This supposition was indicated by single crystal diffraction, Density Functional Theory (DFT) and quantum theory of atoms in molecules (QTAIM) calculations, and concentration-dependent liquid-state 1H nuclear magnetic resonance (NMR). NMR showed that chemical shifts of benzene and pyrazole hydrogens confirm that planar stacking interactions are not formed in solution. The crystalline structures presented different molecular conformations. The molecular structures of 5 and 9b are in a twisted conformation, while compound 7 showed a conformation analogous to a calyx form.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Crystal Structure, and Supramolecular Understanding of 1,3,5-Tris(1-phenyl-1H-pyrazol-5-yl)benzenes

et al. 2017

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“…Subsequently Makhseed et al [80] extended this approach to the synthesis of benzene-1,3,5-trials 104 (R0H) and triethylbenzene-1,3,5-tricarboxylates 104 (R0OH). Recently Al-Zaydi et al were able to affect the conversion of 103d to 104d more efficiently using pyridine hydrochloride as an ionic liquid and MW as the energy source (Scheme 24) [81] refluxing acetic acid reacts to generate 105 only, when the process is carried out in the presence of pyridinium hydrochloride 104e is formed [81]. Very recently, Al-Mousawi et al showed that these conversions can be affected by fusing enaminones in the presence of montmorillonite K10.…”

Section: Solvent-free Reactionsmentioning

confidence: 99%

Green methodologies in organic synthesis: recent developments in our laboratories

Hafez

Al‐Mousawi

Moustafa

et al. 2013

Green Chemistry Letters and Reviews

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The results of the studies carried out in our laboratories during the last 15 years, aimed at developing green methodologies for the synthesis of polyfunctionalized heteroaromatic substances, are surveyed. The results of the investigations demonstrate that green methodologies are not only less hazard than classical preparative methods but they also are more efficient and economical. For example, short reaction times and higher yields are observed for reactions in which conventional heating is replaced by microwave or ultrasound irradiation. The implementation of multicomponent reactions in green preparative routes also reduces the cost of carrying out the reactions because multiple separation and crystallization steps are avoided. In general, by employing the new green methodologies we have been able to produce a large number of polyfunctional aromatic substances in a highly efficient manner.

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“…Microwave energy has been reported to be effective in the synthesis of small molecules in many of our previous works [ 13 , 14 , 15 , 16 ]. However, we noted that microwaves technology is expensive to scale up [ 17 ], in contrast to using “Q-Tube” pressure reactors, which proved to accelerate reactions of negative activation volume in a more optimal and safer manner, compared to microwaves [ 18 ].…”

Section: Introductionmentioning

confidence: 99%

Multi Component Reactions under Increased Pressure: On the Mechanism of Formation of Pyridazino[5,4,3-de][1,6]naphthyridine Derivatives by the Reaction of Malononitrile, Aldehydes and 2-Oxoglyoxalarylhydrazones in Q-Tubes

et al. 2017

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Efficient synthesis of phenanthridin-6(5H)-one derivatives 12a–n in a four-component reaction of aldehyde hydrazone, aromatic aldehydes and malononitrile in Q-Tubes is reported. The results showed that the methodology has the advantage of being a one-pot synthesis of tricyclic systems in good yields. Potential routes leading to formation of compounds 12 are discussed. The structures of the synthesized compounds could be unequivocally established via X-ray crystal structure determination and spectroscopic methods.

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Green technologies in organic synthesis: self-condensation of enamines, enaminones and enaminoesters under microwave irradiation in ionic liquid

Cited by 24 publications

References 21 publications

Synthesis, Crystal Structure, and Supramolecular Understanding of 1,3,5-Tris(1-phenyl-1H-pyrazol-5-yl)benzenes

Synthesis, Crystal Structure, and Supramolecular Understanding of 1,3,5-Tris(1-phenyl-1H-pyrazol-5-yl)benzenes

Green methodologies in organic synthesis: recent developments in our laboratories

Multi Component Reactions under Increased Pressure: On the Mechanism of Formation of Pyridazino[5,4,3-de][1,6]naphthyridine Derivatives by the Reaction of Malononitrile, Aldehydes and 2-Oxoglyoxalarylhydrazones in Q-Tubes

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