An Unexpected Synthesis of 2,3,4‐Trisubstituted Quinolines from Imino‐Isatin and Acetylenic Esters Catalyzed by Pyridine as an Organocatalyst

Afkham, Amir Arian; Mokhtari, Javad; Haghighi, Ali Javaheri; Yavari, Issa

doi:10.1002/slct.201801785

Cited by 9 publications

(3 citation statements)

References 32 publications

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“…Based on the above experimental outcomes and the literature reports,,, we suggested a hypothetical mechanism of the cascade reaction which is shown in Scheme . Presumably, the reaction starts with the formation of salt A by the attack of pyridine moiety of the catalyst to the electron‐deficient acetylene molecule.…”

Section: Resultsmentioning

confidence: 77%

Mesoporous MCM‐41 Silica Supported Pyridine Nanoparticle: A Highly Efficient, Recyclable Catalyst for Expeditious Synthesis of Quinoline Derivatives through Domino Approach

et al. 2019

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A new facile and efficient one-pot three component approach for the preparation of 2, 3, 4-trisubstituted quinolines by (MCM-41)-pyridine catalyzed reaction of easily available substituted isatins and dialkylacetylenedicarboxylates in alcohol has been developed. The (MCM-41)-pyridine nanopowder catalyst has been synthesized and the catalyst has been carefully characterized by various techniques including FT-IR, XRD, HRTEM, EDS, N 2 -adsorption analysis etc. The materials obtained exhibit high surface area and a narrow distribution of mesoporosity.The key features of this methodology are mild reaction conditions, operational simplicity and facile product separation, high to excellent yields, as well as simple catalyst recovery and reusability. The most exciting feature of this cascade reaction is its mechanism involving the unusual ring opening of an isatin moiety, then recyclisation, aromatization followed by esterification. The synthesized substituted quinolines are expected to be used as lead compounds for the development of new drugs.

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Section: Resultsmentioning

confidence: 77%

Mesoporous MCM‐41 Silica Supported Pyridine Nanoparticle: A Highly Efficient, Recyclable Catalyst for Expeditious Synthesis of Quinoline Derivatives through Domino Approach

et al. 2019

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“…2,3,4‐Trisubstituted quinoline derivatives were also prepared via multicomponent reaction (10 examples), by reacting N ‐unsubstituted isatin‐imines (generated in situ through the reaction of isatin with ammonia) and dialkylacetylenedicarboxylates in methanol, at room temperature (Scheme 134D). Pyridine is the organocatalyst employed in this chemical transformation, which affords the desired derivatives in very good yields [275] …”

Section: Non‐oxindole Derivativesmentioning

confidence: 99%

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Brandão

Marques

Carreiro

et al. 2021

The Chemical Record

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Multicomponent reactions (MCRs) are a valuable tool in diversity‐oriented synthesis. Its application to privileged structures is gaining relevance in the fields of organic and medicinal chemistry. Isatin, due to its unique reactivity, can undergo different MCRs, affording multiple interesting scaffolds, namely oxindole‐derivatives (including spirooxindoles, bis‐oxindoles and 3,3‐disubstituted oxindoles) and even, under certain conditions, ring‐opening reactions occur that leads to other heterocyclic compounds. Over the past few years, new methodologies have been described for the application of this important and easily available starting material in MCRs. In this review, we explore these novelties, displaying them according to the structure of the final products obtained.

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“…In this research, as a part of our continued interest in organic synthesis especially using isatin as a strategic substrate for preparation of the 2,3,4-trisubstituted quinoline systems from the reaction between iminoisatin and dialkylacetylenedicarboxylates in MeOH at room temperature in the presence of pyridine as an organocatalyst (29)…”

Section: Introductionmentioning

confidence: 99%

Asymmetric cross-aldol reaction of isatin and ketones catalyzed by crude earthworm extract as efficient biocatalyst

Shams

Aliabad

Rouhani

2020

Green Chemistry Letters and Reviews

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The asymmetric cross-aldol reaction of simple ketones (acetone, cyclohexanone) with isatin derivatives in the presence of crude extract from earthworms as green and effective biocatalyst proceeds easily in MeCN/H 2 O (1:1) as solvent to afford 3-hydroxy-2-oxindoles derivatives. Ten compounds were synthesized in high yields (62-88%) and moderate ee (29-42%). Structure of the synthesized compounds has been characterized on the basis of NMR spectra and CHN analysis. The ee of the obtained compounds was determined by chiral phase HPLC analysis.

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An Unexpected Synthesis of 2,3,4‐Trisubstituted Quinolines from Imino‐Isatin and Acetylenic Esters Catalyzed by Pyridine as an Organocatalyst

Cited by 9 publications

References 32 publications

Mesoporous MCM‐41 Silica Supported Pyridine Nanoparticle: A Highly Efficient, Recyclable Catalyst for Expeditious Synthesis of Quinoline Derivatives through Domino Approach

Mesoporous MCM‐41 Silica Supported Pyridine Nanoparticle: A Highly Efficient, Recyclable Catalyst for Expeditious Synthesis of Quinoline Derivatives through Domino Approach

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Asymmetric cross-aldol reaction of isatin and ketones catalyzed by crude earthworm extract as efficient biocatalyst

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