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Molecules
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Synthetic Studies Aimed at Heterocyclic Organic Compounds
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Synthetic Studies Aimed at Heterocyclic Organic Compounds

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

Deadline for manuscript submissions: 31 May 2024 | Viewed by 34014

Special Issue Editor

Dr. Lee J. Silverberg

E-Mail Website
Guest Editor
Department of Chemistry, Pennsylvania State University, Schuylkill Haven, PA, USA
Interests: organic synthesis; heterocycles; drug discovery

Special Issue Information

Dear Colleagues,

Organic heterocycles are a broad but very important category of molecules. They are widely found in compounds of medicinal and agricultural use. Many of them are considered privileged structures.  They are also biologically important, found in groups, such as nucleic acids and carbohydrates, as well as many other natural products. They are, thus, important targets of synthetic chemistry. This Special Issue will focus on the synthesis of heterocyclic compounds. Papers are welcomed that describe synthesis of specific heterocycles, as well as papers that disclose methods or strategies that could be applied to heterocyclic synthesis. Papers may be articles, communications, or reviews.

Dr. Lee J. Silverberg
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

  • heterocycles
  • synthesis
  • methods
  • medicinal
  • agricultural

Published Papers (5 papers)

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Research

Jump to: Review

22 pages, 2429 KiB  
Article
Desymmetrization of Prochiral N-Pyrazolyl Maleimides via Organocatalyzed Asymmetric Michael Addition with Pyrazolones: Construction of Tri-N-Heterocyclic Scaffolds Bearing Both Central and Axial Chirality
by Jianqi Geng, Xingfu Wei, Biru He, Yuting Hao, Jingping Qu and Baomin Wang
Molecules 2023, 28(11), 4279; https://doi.org/10.3390/molecules28114279 - 23 May 2023
Viewed by 1113
Abstract
The desymmetrization of N-pyrazolyl maleimides was realized through an asymmetric Michael addition by using pyrazolones under mild conditions, leading to the formation of a tri-N-heterocyclic pyrazole–succinimide–pyrazolone assembly in high yields with excellent enantioselectivities (up to 99% yield, up to 99% [...] Read more.
The desymmetrization of N-pyrazolyl maleimides was realized through an asymmetric Michael addition by using pyrazolones under mild conditions, leading to the formation of a tri-N-heterocyclic pyrazole–succinimide–pyrazolone assembly in high yields with excellent enantioselectivities (up to 99% yield, up to 99% ee). The use of a quinine-derived thiourea catalyst was essential for achieving stereocontrol of the vicinal quaternary–tertiary stereocenters together with the C–N chiral axis. Salient features of this protocol included a broad substrate scope, atom economy, mild conditions and simple operation. Moreover, a gram-scale experiment and derivatization of the product further illustrated the practicability and potential application value of this methodology. Full article
(This article belongs to the Special Issue Synthetic Studies Aimed at Heterocyclic Organic Compounds)
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18 pages, 3667 KiB  
Article
Structure and Conformational Mobility of OLED-Relevant 1,3,5-Triazine Derivatives
by Georgi M. Dobrikov, Yana Nikolova, Ivaylo Slavchev, Miroslav Dangalov, Vera Deneva, Liudmil Antonov and Nikolay G. Vassilev
Molecules 2023, 28(3), 1248; https://doi.org/10.3390/molecules28031248 - 27 Jan 2023
Cited by 1 | Viewed by 1680
Abstract
A series of OLED-relevant compounds, consisting of 1,3,5-triazine core linked to various aromatic arms by amino group, has been synthesized and characterized. The studied compounds exist in solution as a mixture of two conformers, a symmetric propeller and asymmetric conformer, in which one [...] Read more.
A series of OLED-relevant compounds, consisting of 1,3,5-triazine core linked to various aromatic arms by amino group, has been synthesized and characterized. The studied compounds exist in solution as a mixture of two conformers, a symmetric propeller and asymmetric conformer, in which one of the aromatic arms is rotated around the C-N bond. At temperatures below −40 °C, the VT NMR spectra in DMF-d7 are in a slow exchange regime, and the signals of two conformers can be elucidated. At temperatures above 100 °C, the VT NMR spectra in DMSO-d6 are in a fast exchange regime, and the averaged spectra can be measured. The ratio of symmetric and asymmetric conformers in DMF-d7 varies from 14:86 to 50:50 depending on the substituents. The rotational barriers of symmetric and asymmetric conformers in DMF-d7 were measured for all compounds and are in the interval from 11.7 to 14.7 kcal/mol. The ground-state energy landscapes of the studied compounds, obtained by DFT calculations, show good agreement with the experimental rotational barriers. The DFT calculations reveal that the observed chemical exchange occurs by the rotation around the C(1,3,5-triazine)-N bond. Although some of the compounds are potentially tautomeric, the measured absorption and emission spectra do not indicate proton transfer neither in the ground nor in the excited state. Full article
(This article belongs to the Special Issue Synthetic Studies Aimed at Heterocyclic Organic Compounds)
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Review

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14 pages, 3394 KiB  
Review
Recent Advances in the Synthesis of the Marine-Derived Alkaloid Fascaplysin and Its Metabolites Homofascaplysins A–C
by Ramana Reddy Mittapalli and Harshita Kumari
Molecules 2024, 29(7), 1590; https://doi.org/10.3390/molecules29071590 - 02 Apr 2024
Viewed by 569
Abstract
The fascaplysin and homofascaplysin class of marine natural products has a characteristic 12H-pyrido[1,2-a:3,4-b′]diindole pentacyclic structure. Fascaplysin was isolated in 1988 from the marine sponge Fascaplysinopsis bergquist sp. The analogs of fascaplysin, such as homofascaplysins A, B, and C, were discovered late in the [...] Read more.
The fascaplysin and homofascaplysin class of marine natural products has a characteristic 12H-pyrido[1,2-a:3,4-b′]diindole pentacyclic structure. Fascaplysin was isolated in 1988 from the marine sponge Fascaplysinopsis bergquist sp. The analogs of fascaplysin, such as homofascaplysins A, B, and C, were discovered late in the Fijian sponge F. reticulate, and also have potent antimicrobial activity and strong cytotoxicity against L-1210 mouse leukemia. In this review, the total synthesis of fascaplysin and its analogs, such as homofascaplysins A, B, and C, will be reviewed, which will offer useful information for medicinal chemistry researchers who are interested in the exploration of marine alkaloids. Full article
(This article belongs to the Special Issue Synthetic Studies Aimed at Heterocyclic Organic Compounds)
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44 pages, 40252 KiB  
Review
Recent Advances in Synthetic Routes to Azacycles
by Anh Thu Nguyen and Hee-Kwon Kim
Molecules 2023, 28(6), 2737; https://doi.org/10.3390/molecules28062737 - 17 Mar 2023
Cited by 2 | Viewed by 1612
Abstract
A heterocycle is an important structural scaffold of many organic compounds found in pharmaceuticals, materials, agrochemicals, and biological processes. Azacycles are one of the most common motifs of a heterocycle and have a variety of applications, including in pharmaceuticals. Therefore, azacycles have received [...] Read more.
A heterocycle is an important structural scaffold of many organic compounds found in pharmaceuticals, materials, agrochemicals, and biological processes. Azacycles are one of the most common motifs of a heterocycle and have a variety of applications, including in pharmaceuticals. Therefore, azacycles have received significant attention from scientists and a variety of methods of synthesizing azacycles have been developed because their efficient synthesis plays a vital role in the production of many useful compounds. In this review, we summarize recent approaches to preparing azacycles via different methods as well as describe plausible reaction mechanisms. Full article
(This article belongs to the Special Issue Synthetic Studies Aimed at Heterocyclic Organic Compounds)
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56 pages, 37176 KiB  
Review
Methods of Lysergic Acid Synthesis—The Key Ergot Alkaloid
by Michał K. Jastrzębski, Agnieszka A. Kaczor and Tomasz M. Wróbel
Molecules 2022, 27(21), 7322; https://doi.org/10.3390/molecules27217322 - 28 Oct 2022
Cited by 8 | Viewed by 28269
Abstract
Ergot is the spore form of the fungus Claviceps purpurea. Ergot alkaloids are indole compounds that are biosynthetically derived from L-tryptophan and represent the largest group of fungal nitrogen metabolites found in nature. The common part of ergot alkaloids is lysergic acid. This [...] Read more.
Ergot is the spore form of the fungus Claviceps purpurea. Ergot alkaloids are indole compounds that are biosynthetically derived from L-tryptophan and represent the largest group of fungal nitrogen metabolites found in nature. The common part of ergot alkaloids is lysergic acid. This review shows the importance of lysergic acid as a representative of ergot alkaloids. The subject of ergot and its alkaloids is presented, with a particular focus on lysergic acid. All methods of total lysergic acid synthesis—through Woodward, Hendrickson, and Szantay intermediates and Heck coupling methods—are presented. The topic of biosynthesis is also discussed. Full article
(This article belongs to the Special Issue Synthetic Studies Aimed at Heterocyclic Organic Compounds)
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