ChemInform Abstract: REAGENTS AND SYNTHETIC METHODS. 23. EASY ONE-FLASK CONVERSION OF AROMATIC ALDEHYDES TO NITRILES

The pyridazinone derivatives, particularly those bearing substituted different group or atom at a different position, have attracted considerable attention due to their characteristic pharmacological and other anticipated activities. These activities promoted the synthesis of a large number of substituted pyridazinone derivatives in order to explore the usefulness of this heterocyclic system. In the present review, various synthetic methods have been studied for the synthesis of substituted pyridazinone derivatives. The behaviour of the pyridazinone toward formaldehyde/piperidine, ethyl chloroacetate, chloroacetic acid, benzene sulfonyl chloride, bromine/acetic acid and aromatic aldehydes has also been studied. However, the reactions of the chloro derivative resulting from the reaction of pyridazinone with phosphorus oxychloride (POCl3). The behavior of chloropyridazine toward hydrazines, thiourea, sodium azide, anthranilic acid, aromatic amines and sulfa compounds have also been taken into consideration. Thethiopyridazinone derivativeswere prepared from the reaction of pyridazinone with phosphorus pentasulphide (P2S5). All the structures of were established on the based of spectroscopic data.

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K2CO3: A Mild and Efficient Catalyst for the Synthesis of Pyran Annulated Heterocyclic Systems by Grinding Method Under Solvent-Free Conditions

Acta Chemica Iasi ◽

10.1515/achi-2017-0014 ◽

2017 ◽

Vol 25 (2) ◽

pp. 163-178 ◽

Cited By ~ 1

Author(s):

Reza Heydari ◽

Rohollah Rahimi ◽

Mehrnoosh Kangani ◽

Afshin Yazdani-Elah-Abadi ◽

Mojtaba Lashkari

Keyword(s):

Room Temperature ◽

Reaction Times ◽

Aromatic Aldehydes ◽

Solvent Free ◽

Synthetic Methods ◽

One Pot ◽

Efficient Catalyst ◽

Grinding Method ◽

Solvent Free Conditions ◽

The One

Abstract The potassium carbonate was applied as a green and efficient catalyst for the one-pot synthesis of pyran annulated heterocyclic systems, via the condensation between aromatic aldehydes, malononitrile and dimedone/1-naphtole by a grinding method at room temperature and solvent-free conditions. Short reaction times, environmentally friendly procedure and excellent yields are the main advantages of this procedure which makes it more economic than other environmentally synthetic methods.

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Reagents and Synthetic Methods 23. Easily One-Flask Conversion of Aromatic Aldehydes to Nitriles

Synthetic Communications ◽

10.1080/00397918308065992 ◽

1983 ◽

Vol 13 (3) ◽

pp. 219-224 ◽

Cited By ~ 13

Author(s):

I. Ganboa ◽

C. Palomo

Keyword(s):

Aromatic Aldehydes ◽

Synthetic Methods

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Microwave-assisted One-pot Synthesis of 7-Dimethylamino-4-Aryl-2- methylamino-3-nitro-4H-chromenes

Letters in Organic Chemistry ◽

10.2174/1570178615666181025114748 ◽

2019 ◽

Vol 16 (6) ◽

pp. 468-473

Author(s):

Pallava Nagaraju ◽

Pannala Padmaja ◽

Pedavenkatagari Narayana Reddy

Keyword(s):

Aromatic Aldehydes ◽

Synthetic Methods ◽

Quinone Methide ◽

Chromatographic Purification ◽

One Pot ◽

Dimethylamino Group ◽

Microwave Assisted ◽

Catalyst Free ◽

One Pot Condensation ◽

Direct Use

4-Aryl-2-amino-4H-chromenes possessing N,N-dimethylamino group have been reported as potential anticancer drugs. Despite few synthetic methods reported in the literature for their synthesis, there appear to be no reports on the direct use of N,N-dimethyl-3-aminophenol for the synthesis of 4- aryl-2-methylamino-3-nitro-4H-chromenes. One-pot condensation of N,N-dimethyl-3-aminophenol, aromatic aldehydes and (E)-N-methyl-1-(methylthio)-2-nitro-ethenamine was carried out using MW irradiation to get the 4-aryl-2-methylamino-3-nitro-4H-chromenes under catalyst-free conditions. This transformation presumably occurs via o-quinone methide formation, Michael addition-intramolecular O-cyclization-elimination sequence of reactions creating new two C-C bonds and one C-O bond. Various substituted aromatic aldehydes reacted smoothly with N,N-dimethyl-3-aminophenol and (E)-Nmethyl- 1-(methylthio)-2-nitro-ethenamine to give the corresponding 4-aryl-2-methylamino-3-nitro-4Hchromenes in good yields. We have developed a one-pot three component condensation of N,Ndimethyl- 3-aminophenol, aromatic aldehyde and NMSM for the synthesis of N,N-dimethylamino substituted 4-aryl-2-methylamino-3-nitro-4H-chromenes in good yields. The significant features of this reaction include catalyst-free, solvent free, no column chromatographic purification, short reaction time and good yields.

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Synthesis, Biological Screening and Docking Study of Some Novel Pyrazolopyrano[2,3-B]quinolin Derivatives as Potent Antibacterial Agents

Current Bioactive Compounds ◽

10.2174/1573407218666220106122432 ◽

2022 ◽

Vol 18 ◽

Author(s):

Hamideh. Emtiazi ◽

Ali Salari Sharif ◽

Mina Ardestani

Keyword(s):

Staphylococcus Aureus ◽

Molecular Docking ◽

Hydrophobic Interactions ◽

Biological Activities ◽

Aromatic Aldehydes ◽

Dna Gyrase ◽

Docking Study ◽

Antibacterial Activities ◽

Synthetic Methods ◽

One Pot

Background: Pyranopyrazoles have a variety of biological activities and can be obtained by various starting materials and synthetic methods. Also, pyrazolopyrano[2,3-b]quinolins that contain pyranopyrazole moiety, have some biological activities such as anti acetylcholinesterase, anti butyrylcholinesterase activity. In this research, our objective is to prepare pyranopyrazole compounds and pyrazolopyrano[2,3-b]quinolins in a simple way and then evaluate their antibacterial effect. Methods: In this study, pyrano[2,3-c]pyrazole derivatives have been synthesized by condensing malononitrile, aromatic aldehydes, and 3-methyl-1-phenyl-2-pyrazolin-5-one in the presence of magnesium perchlorate as a catalyst. Then we prepared pyrazolopyrano[2,3-b]quinolins via subsequent Friedlander reaction between cyclohexanone and the obtained pyrano[2,3-c]pyrazoles. Also, the antimicrobial activity of the synthesized pyrazolopyrano[2,3-b]quinolins against Staphylococcus aureus, Methicillin-resistant Staphylococcus aureus, Pseudomonas aeruginosa, and Escherichia coli were measured. Then we studied molecular docking of them to find the predicted compounds' interactions and binding energy with DNA-gyrase with the AutoDock 4.2 software. Results: Pyrazolopyrano[2,3-b]quinolins were synthesized in optimized conditions. Evaluation of their antibacterial activities showed that these compounds have moderate to good antibacterial activities against four bacteria species. Also molecular docking tests of docked compounds showed a strong bonding interaction with DNA-Gyrase and had been docked into the intercalation place of DNA of DNA-gyrase complex. The molecule bounded to the DNA stabilized by the H bonds, hydrophobic interactions, and π-π interaction. Conclusion: We have developed an efficient and one-pot ecofriendly protocol for the synthesis of some novel pyrano[2,3-c]pyrazol derivatives and pyrazolopyrano[2,3-b]quinolins under simple conditions and then tested them for their antibacterial activities. Also, we studied molecular docking of them. These compounds showed moderate to good inhibitory action.

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