A convenient synthesis and preparation of the derivatives of ethyl-6-(8-hydroxyquinolin-5-yl)-3-methylpyridazine-4-carboxylate as antimicrobial agents

Abdel‐Mohsen, Shawkat A.

doi:10.5155/eurjchem.5.3.517-525.1072

Cited by 5 publications

(8 citation statements)

References 24 publications

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“…After distillation, the free base (137) was crystallised. Its hydrochloride salt was prepared by Burckhalter et al [97]. The reaction conditions for the compounds in Table 6 are almost identical.…”

Section: Syntheses By Using Cyclic Secondary Aminesmentioning

confidence: 99%

“…EtOH with formalin (40%) and then added the aromatic amine in EtOH. Subsequently, the mixture was stirred for 3 h at r.t. and left overnight with the result of 67a-c and 68a-c. An interesting feature is that the Mannich reaction occurred on the side chain rather than on the 8HQ core at position 7 (Scheme 3) [97]. EtOH, reflux, 30-50 h; Yield: 60-70% [96] The transformation of pyridazine-annulated 8HQ was implemented by Abdelmohsen, who treated the solution of 66a or 66b in abs.…”

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confidence: 99%

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confidence: 99%

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Synthesis of Bioactive Aminomethylated 8-Hydroxyquinolines via the Modified Mannich Reaction

Csuvik

Szatmári

2023

IJMS

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8-hydroxyquinoline (oxine) is a widely known and frequently used chelating agent, and the pharmacological effects of the core molecule and its derivatives have been studied since the 19th century. There are several synthetic methods to modify this core. The Mannich reaction is one of the most easily implementable examples, which requires mild reaction conditions and simple chemical reagents. The three components of the Mannich reaction are a primary or secondary amine, an aldehyde and a compound having a hydrogen with pronounced activity. In the modified Mannich reaction, naphthol or a nitrogen-containing naphthol analogue (e.g., 8-hydroxyquinoline) is utilised as the active hydrogen provider compound, thus affording the formation of aminoalkylated products. The amine component can be ammonia and primary or secondary amines. The aldehyde component is highly variable, including aliphatic and aromatic aldehydes. Based on the pharmacological relevance of aminomethylated 8-hydroxyquinolines, this review summarises their syntheses via the modified Mannich reaction starting from 8-hydroxyquinoline, formaldehyde and various amines.

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Section: Syntheses By Using Cyclic Secondary Aminesmentioning

confidence: 99%

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confidence: 99%

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Synthesis of Bioactive Aminomethylated 8-Hydroxyquinolines via the Modified Mannich Reaction

Csuvik

Szatmári

2023

IJMS

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“…DABCO is an organic base that can act as nucleophile and is soluble in water. In continuation of our research program to develop environmentally friendly reactions [19][20][21][22], we report herein a simple, practical, and general three-component reaction for the construction of pyrrole derivatives by the reaction of 5-chloroacetyl-8-hydroxyquinoline, acetylacetone, and aryl-, heteroaryl-, and alkylamines in aqueous medium in the presence of DABCO.…”

Section: Introductionmentioning

confidence: 99%

One-pot synthesis of 5-[1-substituted 4-acetyl-5-methyl-1H-pyrrol-2-yl)]-8-hydroxyquinolines using DABCO as green catalyst

Abdel‐Mohsen

El‐Ossaily

2015

Heterocyclic Communications

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A green and simple method for the synthesis of the title compounds 4 by the reaction of 5-chloroacetyl-8-hydroxyquinoline (1), acetylacetone pentane-2,4-dione (2), and amines 3 in the presence of a catalytic amount of 1,4-diazabicyclo[2.2.2]octane at 60°C is described. The procedure is amenable for the synthesis of other substituted pyrroles. Short reaction time, environmentally friendly procedure, and excellent yields are the main advantages. The structures of products 4a-n were characterized by 1 H NMR, IR, and MS spectra.

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“…[13][14][15][16][17] DABCO is an organic base that can act as a nucleophile. In view of this, and as part of our work on multi-component reactions, [18][19][20][21][22] we here report a simple, practical, and generally three-component reaction for the synthesis of novel indole derivatives by one-pot three-component reaction of 5-chloroacetyl-8-hydroxyquinoline, alkyl-, aryl-and heteroaryl-amines, and dimedone; the reaction is catalyzed by DABCO.…”

Section: Introductionmentioning

confidence: 99%

A facile one-pot synthesis of novel 1-substituted 2-(8-hydroxyquinolin-5-yl)-1,5,6,7-tetrahydro-6,6-dimethyl- 4H-indol-4-one derivatives

Abdel‐Mohsen¹,

El‐Emary²

2016

Arkivoc

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A convenient synthesis and preparation of the derivatives of ethyl-6-(8-hydroxyquinolin-5-yl)-3-methylpyridazine-4-carboxylate as antimicrobial agents

Cited by 5 publications

References 24 publications

Synthesis of Bioactive Aminomethylated 8-Hydroxyquinolines via the Modified Mannich Reaction

Synthesis of Bioactive Aminomethylated 8-Hydroxyquinolines via the Modified Mannich Reaction

One-pot synthesis of 5-[1-substituted 4-acetyl-5-methyl-1H-pyrrol-2-yl)]-8-hydroxyquinolines using DABCO as green catalyst

A facile one-pot synthesis of novel 1-substituted 2-(8-hydroxyquinolin-5-yl)-1,5,6,7-tetrahydro-6,6-dimethyl- 4H-indol-4-one derivatives

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