Ultrasound-Assisted, One-Pot, Four-Component Synthesis of 1,4,6,8-Tetrahydroquinolines in Aqueous Medium

Siddekha, Aisha; Azzam, Sadeq Hamood Saleh; Päsha, M. A.

doi:10.1080/00397911.2013.813545

Cited by 18 publications

(11 citation statements)

References 27 publications

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“…A series of highly substituted 2-amino-1,4,5,6,7,8-hexahydroquinolines-3-carbonitriles (32) were synthesized via ultrasound-assisted, one-pot, four-component condensations of aromatic aldehydes (1), dimedone (13), malononitrile (2) and ammonium acetate (3) using K 2 CO 3 as a catalyst in aqueous medium at ambient temperature (Scheme 9). 99 Scheme 9. Ultrasound-promoted synthesis of 2-amino-1,4,5,6,7,8-hexahydroquinoline-3--carbonitriles in water.…”

Section: Synthesis Of Pyrazolo[34-b]pyridine Derivativesmentioning

confidence: 99%

“…It was also observed that ultrasonic irradiation has a distinct effect on the rate of the reaction. (99) by the condensation between 1,5-aryl-1,4-pentadien-3-one (97) and aminoguanidine hydrochloride (98) using p-dodecylbenzenesulfonic acid (DBSA) as the catalyst in water at ambient temperature. It was well demonstrated that the application of ultrasonic irradiation enhances the reaction rate.…”

Section: Synthesis Of 1-(amidoalkyl)-2-naphthylaminesmentioning

confidence: 99%

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Recent developments on ultrasound-assisted organic synthesis in aqueous medium

Banerjee

2017

JSCS

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In the recent past, a number of methods were reported on the application of ultrasound in organic reactions for the synthesis of diverse organic scaffolds. On the other hand, as far as green chemistry is concerned, water is the safest of all solvents. Thus, a "strong collaboration" between ultrasonic irradiation and aqueous medium holds the key to the development of an environmentally sustainable protocol. The present review summarizes the latest developments in ultrasound-assisted and water-mediated organic synthesis reported to date.

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Section: Synthesis Of Pyrazolo[34-b]pyridine Derivativesmentioning

confidence: 99%

Section: Synthesis Of 1-(amidoalkyl)-2-naphthylaminesmentioning

confidence: 99%

Recent developments on ultrasound-assisted organic synthesis in aqueous medium

Banerjee

2017

JSCS

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“…67 The reaction was performed in water, with K2CO3 catalysis, at room temperature and with short reaction times. Moreover, great yields were achieved for a limited variety of functional groups.…”

Section: D) Ultrasonicationmentioning

confidence: 99%

Synthesis of Quinolines: A Green Perspective

Batista

Pinto

Silva

2016

ACS Sustainable Chem. Eng.

115

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The quinoline scaffold is present in a vast number of natural compounds and pharmacologically active substances, comprising a significant segment of the pharmaceutical market. The classical methods for the synthesis of this heterocyclic skeleton require the use of expensive starting materials and high temperature conditions. Chemists play a fundamental role in the construction of a sustainable future through the pursuit of greener chemical processes. As so, the development of new synthetic methods using more efficient energy sources and less hazardous solvents as well as renewable and eco-friendly catalysts to attain the quinoline scaffold can provide significant environmental and economic advantages. This review unveils green methods used in the synthesis of quinolones. Important green metrics are calculated for each proposed method and the statistical analysis allowed us to propose the best approaches for further investigation. The applied research is eventually unveiling the full potential of Friedländer and/or multicomponent reactions, to improve atom economy. The quinoline structural motif is readily available through a number of classical synthetic routes and from commercially available reagents. The Friedländer synthetic method (A) from ortho-aminoacetophenones (10) and the Skraup (B), Combes (D) and Doebner-Miller (F) syntheses from anilines (11), as well as its adaptations, are good examples. Moreover, the Conrad-Limpach (C), Gould-Jacobs (E) and Camps (G) routes for the synthesis of quinolones are widely used methods (Scheme 1). Still, all classical methods have similar disadvantages, requiring highly acidic and/or oxidizing media, high temperatures and long reaction times.Moreover, most of these synthetic routes present selectivity problems with meta-substituted substrates and its versatility is limited by the reactivity of the methylenic carbon involved in the aldol reaction. 19 Although efficient and versatile, classical routes towards the synthesis of quinolines present serious environmental concerns as most synthetic routes use great excess of a reagents and produce a significant amount of toxic waste.

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“…[24][25] Several homogeneous and heterogeneous catalysts have been employed for the synthesis of substituted hexahydroquinolines derivatives. Among them, the synthesis using nano-ZnO/ultrasound nano-Fe 3 O 4 , [26] AcOH, [27] K 2 CO 3 , [28] triethylamine, [29] Fe 3-x Ti x O 4 @SPDETATSA (N-(3-silyl propyl) diethylene triamine N,N',N''-tri-sulfonic acid immobilized on Fe 3-found to act as laser dyes due to electron delocalization and exhibit fluorescence and laser activity. [33,34] The effectiveness of lasing is dependent upon the substituents at C-9 and N-10 of the acridine chromophore.…”

Section: Introductionmentioning

confidence: 99%

A Green Synthetic Approach Towards One Pot Multi Component Synthesis of Hexahydroquinoline and 9‐Arylhexahydroacridine‐1,8‐dione Derivatives Catalyzed by Sulphonated Rice Husk

2020

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An efficient, straight forward, eco‐friendly procedure for the synthesis of biologically active hexahydroquinoline derivatives and hexahydroacridine‐1,8‐diones has been designed using a novel bio‐degradable heterogeneous catalyst, sulphonated rice‐husk (SRH). SRH provides high density of acid groups making it different from conventional solid acids containing single acid groups. We report an efficient protocol for the synthesis of hexahydroquinolines and hexahydroacridine‐1,8‐diones using this carbon based acid catalyst (SRH) in solvent free and greener solvent respectively. Moreover, operational simplicity, greener reaction condition, reusability of the catalyst, excellent yield (upto 98 %) are the fundamental features of this protocol. The metal free catalyst was characterised using different spectroscopic techniques FTIR, SEM, EDX, Powder XRD, ICP‐AES.

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Ultrasound-Assisted, One-Pot, Four-Component Synthesis of 1,4,6,8-Tetrahydroquinolines in Aqueous Medium

Cited by 18 publications

References 27 publications

Recent developments on ultrasound-assisted organic synthesis in aqueous medium

Recent developments on ultrasound-assisted organic synthesis in aqueous medium

Synthesis of Quinolines: A Green Perspective

A Green Synthetic Approach Towards One Pot Multi Component Synthesis of Hexahydroquinoline and 9‐Arylhexahydroacridine‐1,8‐dione Derivatives Catalyzed by Sulphonated Rice Husk

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