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Recent Progress in Addition Reactions and Organic Synthesis
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Recent Progress in Addition Reactions and Organic Synthesis

A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Physical Chemistry and Chemical Physics".

Deadline for manuscript submissions: 20 April 2025 | Viewed by 3878

Special Issue Editor

Dr. Davor Margetic

E-Mail Website
Guest Editor
Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia
Interests: physical organic chemistry; the development of environmentally friendly organic reactions using modern techniques (extremely high pressures, microwave radiation and mechanochemistry); computational chemistry

Special Issue Information

Dear Colleagues,

Organic synthesis is crucial for the preparation of new carbon-containing compounds that can have various applications: as catalysts, pharmaceuticals, medicinals, modern organic materials, molecular sensors, dyes and pigments, etc. Inspiration for new compounds is often found in nature, by studying and modifying natural products. Organic chemists are constantly searching for better, cheaper, more environmentally friendly, and more efficient ways to make these compounds. Addition reactions, in which upon breaking multiple bonds, new single bonds are formed, are the cornerstone for the synthesis of structurally more complex organic molecules and are widely used. Cycloaddition reactions in particular are recognized as very efficient with a high atom economy, and the current Nobel Prize is awarded for the research and application of bioorthogonal chemistry. Experimental synthetic work is complemented by computational studies that have greatly improved the understanding of the mechanistic details of addition reactions.

The Special Issue "Recent Progress in Addition Reactions and Organic Synthesis" of the International Journal of Molecular Sciences presents the latest experimental and computational efforts of scholars in this area, focusing on the study of molecular mechanisms. In addition to original research articles, review articles on these topics are also welcome.

This Special Issue is dedicated to Professor Ronald N. Warrener on the occasion of his 90th birthday.

Dr. Davor Margetic
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. International Journal of Molecular Sciences is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. There is an Article Processing Charge (APC) for publication in this open access journal. For details about the APC please see here. Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • addition reactions
  • organic synthesis
  • synthesis mechanism

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Published Papers (3 papers)

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Research

15 pages, 7093 KiB  
Article
Synthesis of Novel Benzofuran Spiro-2-Pyrrolidine Derivatives via [3+2] Azomethine Ylide Cycloadditions and Their Antitumor Activity
by Bowen Pan, Tao Wang, Liangliang Zheng, Zhangchao Dong, Lijuan Liu, Xiongwei Liu, Tingting Feng, Ying Zhou and Yang Shi
Int. J. Mol. Sci. 2024, 25(24), 13580; https://doi.org/10.3390/ijms252413580 - 19 Dec 2024
Viewed by 556
Abstract
A synthetic strategy of a three-component spiro-pyrrolidine compound based on benzofuran via an [3+2] azomethine ylide cycloaddition reaction is reported herein. Under mild optimal conditions, this reaction can quickly produce potentially bioactive compounds with a wide range of substrates, high yield, and simple [...] Read more.
A synthetic strategy of a three-component spiro-pyrrolidine compound based on benzofuran via an [3+2] azomethine ylide cycloaddition reaction is reported herein. Under mild optimal conditions, this reaction can quickly produce potentially bioactive compounds with a wide range of substrates, high yield, and simple operation. The desired products were obtained with a yield of 74–99% and a diastereomeric ratio (dr) of >20:1. Subsequently, the inhibitory effects of the compounds on the cell viability of the human cancer cell line HeLa and mouse cancer cell line CT26 were evaluated. Compounds 4b (IC50 = 15.14 ± 1.33 µM) and 4c (IC50 = 10.26 ± 0.87 µM) showed higher antiproliferative activities against HeLa cells than cisplatin (IC50 = 15.91 ± 1.09 µM); compounds 4e (IC50 = 8.31 ± 0.64 µM) and 4s (IC50 = 5.28 ± 0.72 µM) exhibited better inhibitory activities against CT26 cells than cisplatin (IC50 = 10.27 ± 0.71 µM). The introduction of electron-donating substituents was beneficial to the inhibitory activities against cancer cells. Molecular docking simulations revealed that 4e and 4s may exert corresponding bioactivities by binding to antitumor targets through hydrogen bonds, providing a new approach for discovering spiro-heterocyclic antitumor drugs. Full article
(This article belongs to the Special Issue Recent Progress in Addition Reactions and Organic Synthesis)
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12 pages, 7517 KiB  
Article
Theoretical Study of the Mechanism of the Formation of Azomethine Ylide from Isatine and Sarcosine and Its Reactivity in 1,3-Dipolar Cycloaddition Reaction with 7-Oxabenzonorbornadiene
by Ivana Antol, Petar Štrbac, Yasujiro Murata and Davor Margetić
Int. J. Mol. Sci. 2024, 25(12), 6524; https://doi.org/10.3390/ijms25126524 - 13 Jun 2024
Viewed by 1004
Abstract
The reaction mechanism of tthe formation of azomethine ylides from isatins and sarcosine is addressed in the literature in a general manner. This computational study aims to explore the mechanistic steps for this reaction in detail and to assess the reactivity of formed [...] Read more.
The reaction mechanism of tthe formation of azomethine ylides from isatins and sarcosine is addressed in the literature in a general manner. This computational study aims to explore the mechanistic steps for this reaction in detail and to assess the reactivity of formed ylide in a 1,3-dipolar cycloaddition reaction with 7-oxabenzonorbornadiene. For this purpose, density functional theory (DFT) calculations at the M06-2X(SMD,EtOH)/6-31G(d,p) level were employed. The results indicate that CO2 elimination is the rate-determining step, the activation barrier for 1,3-dipolar cycloaddition is lower, and the formed ylide will readily react with dipolarophiles. The substitution of isatine with electron-withdrawal groups slightly decreases the activation barrier for ylide formation. Full article
(This article belongs to the Special Issue Recent Progress in Addition Reactions and Organic Synthesis)
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11 pages, 3751 KiB  
Article
The Effect of Mesoporous Structure of the Support on the Oxidation of Dibenzothiophene
by Ardian Nurwita and Maciej Trejda
Int. J. Mol. Sci. 2023, 24(23), 16957; https://doi.org/10.3390/ijms242316957 - 29 Nov 2023
Cited by 3 | Viewed by 1581
Abstract
A source of Brønsted acid centers, generated on the surface of two mesoporous silica supports of different structures (SBA-15 and MCF), was 3-(trihydroxysilyl)-1-propanesufonic acid (TPS). The materials obtained were characterized and applied as catalysts for the oxidative desulfurization of dibenzothiophene (DBT) with hydrogen [...] Read more.
A source of Brønsted acid centers, generated on the surface of two mesoporous silica supports of different structures (SBA-15 and MCF), was 3-(trihydroxysilyl)-1-propanesufonic acid (TPS). The materials obtained were characterized and applied as catalysts for the oxidative desulfurization of dibenzothiophene (DBT) with hydrogen peroxide as a model ODS (oxidative desulfurization) process. The properties of the materials were examined via nitrogen physisorption, XRD (X-ray Diffraction) and elemental analysis showing the preservation of the support structure after modification with organosilane species. Due to the aggregation of catalyst particles in the reaction mixture, the SBA-15 based catalyst was not very effective in DBT oxidation. Contrary, TPS/MCF catalyst exhibited a very good activity (almost total conversion of DBT after 1 h in optimized reaction conditions) and stability in dibenzothiophene oxidation in mild reaction conditions. Full article
(This article belongs to the Special Issue Recent Progress in Addition Reactions and Organic Synthesis)
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