Experimental and computational studies on the synthesis of diastereoselective natural-based Meldrum spiro dibenzofuran derivatives

Dastoorani, Parvaneh; Khalilzadeh, Mohammad A.; Khaleghi, Fatemeh; Maghsoodlou, Malek Taher; Kaminsky, Werner; Rad, Ali Shokuhi

doi:10.1039/c9nj00766k

Cited by 7 publications

(4 citation statements)

References 40 publications

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“…In 2019, the one‐pot multi‐component reaction between euparin 180 , aldehyde 13 , and Meldrum's acid 1 was developed by Dastoorani and co‐workers to produce Meldrum spiro dibenzofuran derivatives ( spiro [1‐(3‐hydroxy‐6‐methyl‐8‐phenyl‐7,7,8,9 a ‐tetrahydrodibenzofuran‐2‐yl)‐ethanone(2,2‐dimethyl[1,3] dioxane‐4,6‐dione)]) 181 , which displayed excellent diastereo and regioselectivity (Scheme 78). [79] …”

Section: Other Miscellaneous Compoundsmentioning

confidence: 99%

“…In 2019, the one-pot multi-component reaction between euparin 180, aldehyde 13, and Meldrum's acid 1 was developed by Dastoorani and co-workers to produce Meldrum spiro dibenzofuran derivatives (spiro[1-(3-hydroxy-6methyl-8-phenyl-7,7,8,9a-tetrahydrodibenzofuran-2-yl)ethanone(2,2-dimethyl [1,3] dioxane-4,6-dione)]) 181, which displayed excellent diastereo and regioselectivity (Scheme 78). [79] A greener MCR was developed by Patil and co-workers to prepare spiro-fused heterocycles 183 (Scheme 79) exploiting the use of urea 182, aryl aldehydes 13, and Meldrum's acid 1 in the presence of polymer gel-entrapped catalyst. [80] A possible mechanistic for ZnCl In 2021, Rajeev and co-workers designed the reaction of indoles 33, Meldrum's acid 1, and aldehydes 13 in DMF at room temperature followed by decarboxylation by EtOH/ H 2 O/amines as a nucleophile to afford the indole-3-propranoates/propanoic acid/propanamides 184 (Scheme 81).…”

Section: Other Miscellaneous Compoundsmentioning

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: Other Miscellaneous Compoundsmentioning

confidence: 99%

Section: Other Miscellaneous Compoundsmentioning

confidence: 99%

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

Ziarani,

Ebrahimi,

Mohajer

et al. 2023

ChemistrySelect

View full text Add to dashboard Cite

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“…3,4 Due to the advantages mentioned above, developing new MCRs with environmentally benign protocols has been recognized as one of the most important topics in synthetic chemistry. [5][6][7] MCRs display many of the most desired features for an organic synthesis, [8][9][10] and they have been intensively studied in recent years. [11][12][13][14] Heterocyclic rings are the fundamental components in the skeleton of more than half of the biologically active compounds produced by nature.…”

Section: Introductionmentioning

confidence: 99%

Three-component reaction involving isoquinoline and dimethyl acethylenedicarboxylate in the presence of indole: Theoretical and experimental investigations of the reaction mechanism

Zakarianezhad

Habibi‐Khorassani

Makiabadi

et al. 2021

Progress in Reaction Kinetics and Mechanism

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The reaction kinetics among isoquinoline, dimethyl acetylenedicarboxylate, and indole (as NH-acid) were investigated using ultraviolet (UV) spectrophotometry. The reaction rate equation was obtained, the dependence of the reaction rate on different reactants was determined, and the overall rate constant ( kov) was calculated. By studying the effects of solvent, temperature, and concentration on the reaction rate, some useful information was obtained. A logical mechanism consistent with the experimental observations was proposed. Also, comprehensive theoretical studies were performed to evaluate the potential energy surfaces of all structures that participated in the reaction mechanism. Finally, the proposed mechanism was confirmed by the obtained results and the probable and logical reaction paths and also a correct product configuration were suggested based on the theoretical results.

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“…[22] To the best of the authors' knowledge, this is the first study of the quantum-based parameters of the thiolation of a nucleotide and its adsorption on metallic nanoparticles. Because of the successful application of DFT in finding the mechanism of interaction, [23][24][25][26][27][28][29] we used this methodology for the full optimization of all structures in water, acetonitrile, and the gas phase to determine the accuracy of the mechanism of interaction. AMP as a representative of the nucleotide family was considered to be a short form of DNA or RNA molecules.…”

Section: Introductionmentioning

confidence: 99%

Computational investigation of the strategy of DNA/RNA stabilization through the study of the conjugation of an oligonucleotide with silver and gold nanoparticles

Aali

Rad

Esfahanian

2020

Applied Organom Chemis

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This research deals with the potential of metallic nanoparticles in DNA/RNA stabilization. In this regard, the interaction of adenosine monophosphate (AMP) as a representative of the nucleotide family was theoretically investigated through density functional theory. AMP is a short form of DNA or RNA macromolecules that can interact with gold (Au) and silver (Ag) nanoparticles. The literature represents the thiolation of oligonucleotides as a suitable way for DNA/RNA adsorption on the stated nanoparticles. In this study, the role of different solvents on the thiolation of AMP is scrutinized. The results showed that acetonitrile is the best solvent for the thiolation of AMP with reaction enthalpy (ΔH) of −66.3 kJ/mol. The adsorption of thiolated adenosine monophosphate (TAMP) on the surface of Ag/Au nanoparticles (Ag/AuNP) was studied in different solvents, and in the gas phase. Our results revealed the interaction of TAMP with adsorption energies of −65.3 and −74.1 kJ/mol (gas phase), −54.8 and −62.5 kJ/mol (acetonitrile), and −59.2 and −70.6 kJ/mol (water) on AgNPs and AuNPs, respectively. AuNPs have a shorter bond distance in adsorption of TAMP compared to AgNPs (2.61 vs. 2.78 Å). For all systems, the frontier molecular orbital, the electronic charge passed through the nanoparticles, the density of states, and the molecular electrostatic potential were investigated. The results confirm the suitability of these nanoparticles as carriers for nucleotides that may be useful in gen delivery applications.

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Experimental and computational studies on the synthesis of diastereoselective natural-based Meldrum spiro dibenzofuran derivatives

Cited by 7 publications

References 40 publications

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

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

Three-component reaction involving isoquinoline and dimethyl acethylenedicarboxylate in the presence of indole: Theoretical and experimental investigations of the reaction mechanism

Computational investigation of the strategy of DNA/RNA stabilization through the study of the conjugation of an oligonucleotide with silver and gold nanoparticles

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