Formation of trialkyl quinoline-2,3,4-tricarboxylates by reaction of isatin, dialkyl acetylenedicarboxylates, and sodium O-alkyl carbonodithioates

Yavari, Issa; Seyfi, Samereh; Hossaini, Zinatossadat

doi:10.1016/j.tetlet.2010.02.107

Cited by 37 publications

(13 citation statements)

References 19 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: 99%

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: 99%

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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“…The annulation of 101 leads to the formation of intermediate 102 , which undergoes dehydration to give intermediates 103 . The addition of sodium alkylates to 103 and subsequent elimination of carbon disulfide and sodium alkylate leads to the production of 99 via intermediates 104 51…”

Section: Miscellaneous Isatin‐based Mcrsmentioning

confidence: 99%

Recent Advances in Diversity Oriented Synthesis through Isatin‐based Multicomponent Reactions

2013

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Isatins are well‐known carbonyl electrophiles which allow a vast number of reactions initiated by nucleophilic attack on the C3 carbonyl group when used as starting materials. The most notable feature of isatins is that they serve as donors of oxindole fragments and furnish spirocyclic products in most cases. Because of their high reactivity and easy availability, isatins have been broadly used as building blocks in the synthesis of structurally complex and diverse heterocyclic compounds in multicomponent reactions (MCRs). Recent advances in diversity oriented synthesis with isatin‐based MCRs are discussed in this Focus Review and are classified into different sections based on the key transformation involved in the reactions, such as 1,3‐dipolar cycloaddition, Knoevenagel reaction, ring‐opening of isatins and so on.

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“… 2 Consequently, a variety of novel and expeditious approaches for the preparation of a diverse range of substituted quinolines have been developed. 3 The quinoline scaffold has even been described as a “privileged structure”, since members of this structural class are able to interact with different types of bioactive targets and have attracted the interest of investigators in a broad spectrum of sciences from chemistry and biology to medicine. 4 Hence, introducing quinoline derivatives into bioactive molecules in the late-stage functionalization of natural products and drugs under mild conditions is of equal importance to the direct synthesis of quinolines in the field of chemical biology and pharmacology.…”

Section: Introductionmentioning

confidence: 99%

Paired electrolysis enabled annulation for the quinolyl-modification of bioactive molecules

You

Ruan

et al. 2022

Chem. Sci.

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Formation of trialkyl quinoline-2,3,4-tricarboxylates by reaction of isatin, dialkyl acetylenedicarboxylates, and sodium O-alkyl carbonodithioates

Cited by 37 publications

References 19 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

Recent Advances in Diversity Oriented Synthesis through Isatin‐based Multicomponent Reactions

Paired electrolysis enabled annulation for the quinolyl-modification of bioactive molecules

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