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Novel Organic Synthesis and Synthetic Methods
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Novel Organic Synthesis and Synthetic Methods

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (31 December 2022) | Viewed by 5778

Special Issue Editor

Dr. Jiří Pospíšil

E-Mail Website
Guest Editor
Department of Chemical Biology & Department of Organic Chemistry, Palacky University, and Laboratory of Growth Regulators, Institute of Experimental Botany of the Academy of Sciences of the Czech Republic, Prague, Czech Republic
Interests: natural product synthesis; synthetic method development; organocatalysis; plant secondary metabolites

Special Issue Information

Dear Colleagues,

This Special Issue is entitled “Novel Organic Synthesis and Synthetic Methods”. The development of new synthetic methods and methodologies is one of the key features of modern organic synthesis. Novel and stereoselective ways of C–C and C–heteroatom bond-forming reactions are of considerable importance when the selected type of bond needs to be made within the targeted molecule. The criteria of such bond-forming reaction, however, can vary tremendously. The demands placed on individual transformations will vary according to the purpose for which they are intended to be used. Indeed, a medicinal chemist will require different types of transformation with regard to chemical yields, chemoselectivity, or atom efficiency, when compared to a process chemist or a Ph.D. student that carries out total synthesis in the academic environment. This means that no developed synthetic methodology is better or worse, only more or less suitable for its purpose. This Special Issue will cover novel synthetic methods and methodologies developed as new ways to synthesize defined classes of substances. However, all included methods and methodologies should be evaluated in terms of their scope and limitations.

Dr. Jiří Pospíšil
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. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). 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

  • synthetic methods
  • stereoselective reactions
  • novel transformations
  • C–C bond-forming reactions
  • C–heteroatom forming reactions
  • targeted synthesis
  • chemoselective transformations

Published Papers (3 papers)

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Research

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11 pages, 960 KiB  
Article
A Comparative Study of the Synthesis and Hydrolysis of sym-Triaminobenzene Homologues
by Irina A. Shchurova, Natalia A. Alekseyeva, Sergey V. Sysolyatin and Valeriy V. Malykhin
Molecules 2022, 27(23), 8595; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27238595 - 06 Dec 2022
Viewed by 1036
Abstract
Here, we investigated the synthetic processes for the methyl derivatives of sym-triaminobenzene and phloroglucinol, the essential chemical reactants coming into use in the production of dyes and pigments, and medicinal drugs for different purposes. The most eco-benign process for the synthesis of triamino [...] Read more.
Here, we investigated the synthetic processes for the methyl derivatives of sym-triaminobenzene and phloroglucinol, the essential chemical reactants coming into use in the production of dyes and pigments, and medicinal drugs for different purposes. The most eco-benign process for the synthesis of triamino derivatives involves the catalytic hydrogenation of corresponding nitroarenes. The present study investigated the hydrogenation of 2,4,6-trinitrotoluene, 2,4,6-trinitroxylene, and 2,4,6-trinitromesitylene over a Pd catalyst. A 1% Pd/Sibunit catalyst was found to be preferable to the 5% analogue with a preserved palladium loading because it shortens the reaction time and provides a higher yield of the target product. The hydrogenation in methanol (or mixed methanol/toluene) at 50–55 °C and 0.5 MPa pressure produced 2,4,6-triaminotoluene, 2,4,6-triaminoxylene, and 2,4,6-triaminomesitylene, which were isolated as sulfuric acid salts in 98, 91, and 97% yields, respectively. The hydrolysis process of the resultant salts was examined, and conditions leading to mono-, di-, and trimethyl derivatives of phloroglucinol (90, 77, and 82%, respectively,) were identified. The hydrogenation of the trinitrobenzene homologues in mixed 7:1 (v/v) acetone/water, followed by hydrolysis to the respective polyphenols, was explored. A successful result was achieved only for 2,4,6-trinitrotoluene. The catalyst activity was shown to decline negligibly throughout 10 cycles of reuse. 2-Methylphloroglucinol was synthesized in a high yield ranging from 85 to 91% calculated as 2,4,6-trinitrotoluene. Full article
(This article belongs to the Special Issue Novel Organic Synthesis and Synthetic Methods)
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15 pages, 2031 KiB  
Article
Total Synthesis of 6-Deoxydihydrokalafungin, a Key Biosynthetic Precursor of Actinorhodin, and Its Epimer
by Takuya Kumamoto, Mika Kainuma, Azusa Takahashi, Yoshika Matsuo, Kazuaki Katakawa, Takaaki Taguchi and Koji Ichinose
Molecules 2021, 26(21), 6397; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26216397 - 22 Oct 2021
Cited by 3 | Viewed by 1741
Abstract
In this article, we report the total synthesis of 6-deoxydihydrokalafungin (DDHK), a key biosynthetic intermediate of a dimeric benzoisochromanequinone antibiotic, actinorhodin (ACT), and its epimer, epi-DDHK. Tricyclic hemiacetal with 3-siloxyethyl group was subjected to Et3SiH reduction to establish the 1,3- [...] Read more.
In this article, we report the total synthesis of 6-deoxydihydrokalafungin (DDHK), a key biosynthetic intermediate of a dimeric benzoisochromanequinone antibiotic, actinorhodin (ACT), and its epimer, epi-DDHK. Tricyclic hemiacetal with 3-siloxyethyl group was subjected to Et3SiH reduction to establish the 1,3-cis stereochemistry in the benzoisochromane, and a subsequent oxidation/deprotection sequence then afforded epi-DDHK. A bicyclic acetal was subjected to AlH3 reduction to deliver the desired 1,3-trans isomer in an approximately 3:1 ratio, which was subjected to a similar sequence to that used for the 1,3-cis isomer that successfully afforded DDHK. A semisynthetic approach from (S)-DNPA, an isolable biosynthetic precursor of ACT, was also examined to afford DDHK and its epimer, which are identical to the synthetic products. Full article
(This article belongs to the Special Issue Novel Organic Synthesis and Synthetic Methods)
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Review

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19 pages, 2373 KiB  
Review
Recent Advances in the Heterogeneous Photocatalytic Hydroxylation of Benzene to Phenol
by Weiwei Han, Wei Xiang, Jun Shi and Yue Ji
Molecules 2022, 27(17), 5457; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27175457 - 25 Aug 2022
Cited by 11 | Viewed by 2109
Abstract
Phenol is an important chemical material that is widely used in industry. Currently, phenol is dominantly produced by the well-known three-step cumene process, which suffers from severe drawbacks. Therefore, developing a green, sustainable, and economical strategy for the production of phenol directly from [...] Read more.
Phenol is an important chemical material that is widely used in industry. Currently, phenol is dominantly produced by the well-known three-step cumene process, which suffers from severe drawbacks. Therefore, developing a green, sustainable, and economical strategy for the production of phenol directly from benzene is urgently needed. In recent years, the photocatalytic hydroxylation of benzene to phenol, which is economically feasible and could be performed under mild conditions, has attracted more attention, and development of highly efficient photocatalyst would be a key issue in this field. In this review, we systematically introduce the recent achievements of photocatalytic hydroxylation of benzene to phenol from 2015 to mid-2022, and various heterogeneous photocatalysts are comprehensively reviewed, including semiconductors, polyoxometalates (POMs), graphitic carbon nitride (g-C3N4), metal–organic frameworks (MOFs), carbon materials, and some other types of photocatalysts. Much effort is focused on the physical and chemical approaches for modification of these photocatalysts. The challenges and future promising directions for further enhancing the catalytic performances in photocatalytic hydroxylation of benzene are discussed in the end. Full article
(This article belongs to the Special Issue Novel Organic Synthesis and Synthetic Methods)
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