Design, synthesis, and molecular docking of new 5-HT reuptake inhibitors based on modified 1,2-dihydrocyclopenta[b]indol-3(4H)-one scaffold

Szewczyk, Milena; Punda, Paweł; Janikowska, Karolina; Makowiec, Sławomir

doi:10.1007/s12039-019-1621-x

Cited by 4 publications

(2 citation statements)

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“…[72] Synthesis of 5-((1H-indol-3-yl)(aryl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-diones 160 was reported by Szewczyk and co-workers through the MCR between N-methylindole 159, benzaldehydes 13, and Meldrum's acid 1 catalyzed by Lproline in acetonitrile (Scheme 72). [73] A catalyst-free method for the preparation of Knoevenogel-Michael adducts of imidazole derivatives 162 via a three-component reaction of aromatic aldehydes 13 with Meldrum's acid 1 and 2-amino-4-arylimidazoles 161 in refluxing 2-propranol for 3-5 minutes was reported by Lipson and co-workers (Scheme 73). [74] Khopade and co-workers reported the enantioselective reaction of aldehyde 13, ketone 163-164, and Meldrum's acid 1 to produce enantiopure-δ-keto Meldrum's acid 165-166 (Scheme 74) wherein Cinchona-based primary amine was used as an organocatalyst in this MCR.…”

Section: Synthesis Of 5-monosubstituted Meldrum's Acidsmentioning

confidence: 99%

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The Molecular Diversity Scope of Meldrum's Acid in Multicomponent Reactions

Ziarani,

Ebrahimi,

Mohajer

et al. 2023

ChemistrySelect

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Multicomponent reactions (MCRs) have gained significant attention in the field of organic synthesis due to their ability to efficiently construct complex molecular structures in a single step. Among the reagents employed in MCRs, Meldrum's acid has emerged as a highly versatile and valuable starting material, offering a wide range of molecular diversity. This comprehensive review explores the molecular diversity scope of Meldrum's acid in various MCRs, focusing on its unique attributes and the greener aspects of its application. Meldrum's acid possesses several remarkable features that contribute to its suitability as a key component in MCRs. Its high acidity enables effective participation in a variety of chemical reactions, while its rigid structure provides stability and allows for precise control of the reaction pathways. Furthermore, the ability of Meldrum's acid to undergo both nucleophilic and electrophilic attacks makes it highly versatile in the construction of diverse molecular frameworks. Its low steric hindrance further enhances its reactivity, facilitating efficient bond formation. By surveying the literature from the last five years (2018–2022), we delve into the broad range of applications of Meldrum's acid in MCRs. The review encompasses the synthesis of various heterocyclic compounds, highlighting the significance of Meldrum's acid in achieving molecular diversity. Moreover, particular emphasis is placed on the greener aspects of utilizing Meldrum's acid, considering the growing demand for environmentally friendly synthetic approaches. This includes exploring greener solvents, milder reaction conditions, and reduced waste generation.

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Section: Synthesis Of 5-monosubstituted Meldrum's Acidsmentioning

confidence: 99%

“…Synthesis of 5‐((1 H ‐indol‐3‐yl)(aryl)methyl)‐2,2‐dimethyl‐1,3‐dioxane‐4,6‐diones 160 was reported by Szewczyk and co‐workers through the MCR between N ‐methylindole 159 , benzaldehydes 13 , and Meldrum's acid 1 catalyzed by L‐proline in acetonitrile (Scheme 72). [73] …”

Section: Synthesis Of 5‐monosubstituted Meldrum's Acidsmentioning

confidence: 99%

The Molecular Diversity Scope of Meldrum's Acid in Multicomponent Reactions

Ziarani,

Ebrahimi,

Mohajer

et al. 2023

ChemistrySelect

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One-Pot Multicomponent Synthesis, Antibacterial and Antiproliferative Evaluation of Indole Derivatives

2023

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Meldrum’s acid assisted formation of tetrahydroquinolin-2-one derivatives a short synthetic pathway to the biologically useful scaffold

Ryczkowska,

Trocka,

Hromova

et al. 2024

Sci Rep

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A new method for the preparation of tetrahydroquinolin-2-one derivatives is presented. This approach involves a two-step reaction between enaminones and acylating agents, immediately followed by electrophilic cyclization, all within a single synthesis procedure, eliminating the need to isolate intermediates. The entire process is facilitated by the use of acyl Meldrum’s acids which not only shortens the preparation time of the substrates but also easily extends the range of substituents That can be used. The method’s scope and limitations were evaluated with various reagent combinations thus demonstrating its general applicability to the synthesis of tetrahydroquinolin-2-one core. Interestingly, some exceptions to the regular reaction pathway were observed when a strong EDG (electron donating group) was introduced via acyl Meldrum’s acids. The underlying mechanism of this phenomenon was elucidated during the investigation.

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Design, synthesis, and molecular docking of new 5-HT reuptake inhibitors based on modified 1,2-dihydrocyclopenta[b]indol-3(4H)-one scaffold

Cited by 4 publications

References 50 publications

The Molecular Diversity Scope of Meldrum's Acid in Multicomponent Reactions

The Molecular Diversity Scope of Meldrum's Acid in Multicomponent Reactions

One-Pot Multicomponent Synthesis, Antibacterial and Antiproliferative Evaluation of Indole Derivatives

Meldrum’s acid assisted formation of tetrahydroquinolin-2-one derivatives a short synthetic pathway to the biologically useful scaffold

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