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Synthesis and Properties of Heterocyclic Compounds: Recent Advances
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Synthesis and Properties of Heterocyclic Compounds: Recent Advances

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

Deadline for manuscript submissions: 31 October 2024 | Viewed by 3973

Special Issue Editors

Dr. Yong You

E-Mail Website
Guest Editor
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, China
Interests: asymmetric catalysis; radical chemistry; synthesis of chiral organic functional materials
Dr. Zhen Hua Wang

E-Mail Website
Guest Editor
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, China
Interests: organic synthesis methodologies; metal-mediated asymmetric catalysis; asymmetric organocatalysis; radical chemistry; total synthesis of optically active pharmaceuticals

Special Issue Information

Dear Colleagues,

Heterocyclic compounds are products abundant in nature and have wide applications in pharmaceuticals, agrochemicals, and materials science. The presence of heteroatoms in their structure gives them distinctive properties and reactivity. These compounds often exhibit different electronic and steric effects compared to their homocyclic counterparts, which can significantly impact their biological activity and chemical reactivity. The efficient construction and property research of heterocyclic compounds have always been increasingly important foci for organic synthesis chemists and pharmacologists.

In this context, the primary objective of this Special Issue, entitled “Synthesis and Properties of Heterocyclic Compounds: Recent Advances”, is to gather recent advances on heterocyclic compounds. We sincerely invite researchers and scholars in the fields of chemistry and pharmaceuticals to contribute to this Special Issue on heterocyclic compounds. Your valuable research work and insights will greatly contribute to the advancement of knowledge in this area. We look forward to receiving your submissions of original research articles or reviews reporting on current advances. This Special Issue’s topics of interest include, but are not limited to, novel synthetic approaches, applications, and biological activity research.

Dr. Yong You
Dr. Zhen Hua Wang
Guest Editors

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
  • catalysis
  • organic synthesis
  • cascade cyclization
  • cycloaddition
  • biological activity
  • natural products

Published Papers (6 papers)

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Research

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21 pages, 2955 KiB  
Article
Synthesis of 5-(Aryl)amino-1,2,3-triazole-containing 2,1,3-Benzothiadiazoles via Azide–Nitrile Cycloaddition Followed by Buchwald–Hartwig Reaction
by Pavel S. Gribanov, Anna N. Philippova, Maxim A. Topchiy, Dmitry A. Lypenko, Artem V. Dmitriev, Sergey D. Tokarev, Alexander F. Smol’yakov, Alexey N. Rodionov, Andrey F. Asachenko and Sergey N. Osipov
Molecules 2024, 29(9), 2151; https://doi.org/10.3390/molecules29092151 - 06 May 2024
Viewed by 231
Abstract
An efficient access to the novel 5-(aryl)amino-1,2,3-triazole-containing 2,1,3-benzothiadiazole derivatives has been developed. The method is based on 1,3-dipolar azide–nitrile cycloaddition followed by Buchwald–Hartwig cross-coupling to afford the corresponding N-aryl and N,N-diaryl substituted 5-amino-1,2,3-triazolyl 2,1,3-benzothiadiazoles under NHC-Pd catalysis. The one-pot [...] Read more.
An efficient access to the novel 5-(aryl)amino-1,2,3-triazole-containing 2,1,3-benzothiadiazole derivatives has been developed. The method is based on 1,3-dipolar azide–nitrile cycloaddition followed by Buchwald–Hartwig cross-coupling to afford the corresponding N-aryl and N,N-diaryl substituted 5-amino-1,2,3-triazolyl 2,1,3-benzothiadiazoles under NHC-Pd catalysis. The one-pot diarylative Pd-catalyzed heterocyclization opens the straightforward route to triazole-linked carbazole-benzothiadiazole D-A systems. The optical and electrochemical properties of the compound obtained were investigated to estimate their potential application as emissive layers in OLED devises. The quantum yield of photoluminescence (PLQY) of the synthesized D-A derivatives depends to a large extent on electron-donating strengths of donor (D) component, reaching in some cases the values closed to 100%. Based on the most photoactive derivative and wide bandgap host material mCP, a light-emitting layer of OLED was made. The device showed a maximum brightness of 8000 cd/m2 at an applied voltage of 18 V. The maximum current efficiency of the device reaches a value of 3.29 cd/A. Full article
(This article belongs to the Special Issue Synthesis and Properties of Heterocyclic Compounds: Recent Advances)
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15 pages, 1589 KiB  
Communication
Dearomatization of 3-Aminophenols for Synthesis of Spiro[chromane-3,1′-cyclohexane]-2′,4′-dien-6′-ones via Hydride Transfer Strategy-Enabled [5+1] Annulations
by Jia-Cheng Ge, Yufeng Wang, Feng-Wei Guo, Xiangyun Kong, Fangzhi Hu and Shuai-Shuai Li
Molecules 2024, 29(5), 1012; https://doi.org/10.3390/molecules29051012 - 26 Feb 2024
Viewed by 520
Abstract
The Sc(OTf)3-catalyzed dearomative [5+1] annulations between readily available 3-aminophenols and O-alkyl ortho-oxybenzaldehydes were developed for synthesis of spiro[chromane-3,1′-cyclohexane]-2′,4′-dien-6′-ones. The “two-birds-with-one-stone” strategy was disclosed by the dearomatization of phenols and direct α-C(sp3)–H bond functionalization of oxygen through cascade [...] Read more.
The Sc(OTf)3-catalyzed dearomative [5+1] annulations between readily available 3-aminophenols and O-alkyl ortho-oxybenzaldehydes were developed for synthesis of spiro[chromane-3,1′-cyclohexane]-2′,4′-dien-6′-ones. The “two-birds-with-one-stone” strategy was disclosed by the dearomatization of phenols and direct α-C(sp3)–H bond functionalization of oxygen through cascade condensation/[1,5]-hydride transfer/dearomative-cyclization process. In addition, the antifungal activity assay and derivatizations of products were conducted to further enrich the utility of the structure. Full article
(This article belongs to the Special Issue Synthesis and Properties of Heterocyclic Compounds: Recent Advances)
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12 pages, 2602 KiB  
Communication
A Facile Ugi/Ullmann Cascade Reaction to Access Fused Indazolo-Quinoxaline Derivatives with Potent Anticancer Activity
by Yong Li, Liujun He, Hongxia Qin, Yao Liu, Binxin Yang, Zhigang Xu and Donglin Yang
Molecules 2024, 29(2), 464; https://doi.org/10.3390/molecules29020464 - 17 Jan 2024
Viewed by 778
Abstract
A facile methodology for the construction of a complex heterocycle indazolo-fused quinoxalinone has been developed via an Ugi four-component reaction (U-4CR) followed by an intramolecular Ullmann reaction. The expeditious process features an operationally simple approach, time efficiency, and a broad substrate scope. Biological [...] Read more.
A facile methodology for the construction of a complex heterocycle indazolo-fused quinoxalinone has been developed via an Ugi four-component reaction (U-4CR) followed by an intramolecular Ullmann reaction. The expeditious process features an operationally simple approach, time efficiency, and a broad substrate scope. Biological activity was evaluated and demonstrated that compound 6e inhibits human colon cancer cell HCT116 proliferation with an IC50 of 2.1 μM, suggesting potential applications for developing a drug lead in medicinal chemistry. Full article
(This article belongs to the Special Issue Synthesis and Properties of Heterocyclic Compounds: Recent Advances)
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22 pages, 7715 KiB  
Article
Synthesis of Seven Indolizine-Derived Pentathiepines: Strong Electronic Structure Response to Nitro Substitution in Position C-9
by Roberto Tallarita, Lukas Manuel Jacobsen, Benedict J. Elvers, Stefan Richter, Siva S. M. Bandaru, Jevy V. Correia and Carola Schulzke
Molecules 2024, 29(1), 216; https://doi.org/10.3390/molecules29010216 - 30 Dec 2023
Viewed by 742
Abstract
Seven new 1,2,3,4,5-pentathiepino[6,7-a]indolizines were synthesized in which the pentathiepine moieties bear an indolizine backbone that is derivatized from C–H to F-, Cl-, Br-, I-, NO2-, and CH3-substitutions, respectively, in a meta position relative to the aza group [...] Read more.
Seven new 1,2,3,4,5-pentathiepino[6,7-a]indolizines were synthesized in which the pentathiepine moieties bear an indolizine backbone that is derivatized from C–H to F-, Cl-, Br-, I-, NO2-, and CH3-substitutions, respectively, in a meta position relative to the aza group on the pyridine moiety. Their preparation took place via two common steps: (i) a Sonogashira coupling between (4-substituted) 2-bromo- or 2-chloropyridines and propynyl 3,3-diethylacetal, and (ii) a ring closing reaction mediated by a molybdenum oxo-bistetrasulfido complex and elemental sulfur. The latter simultaneously facilitates the 1,2,3,4,5-pentathiepino chain/ring- and indolizine ring-formations. The fluoro derivative was addressed with 2-bromo-5-aminopyridine as the starting material via a Sandmeyer reaction. The iodo derivative was obtained from 5-bromo-2-alkynylpiridine using a metal-assisted variation of the Finkelstein reaction. The requirement to explore different reaction conditions and the varied respective yields of the final products are discussed. The influence of the distinct substitutions on the pyridine moieties, their electronic structures, and respective chemical properties was investigated through a set of spectroscopic/analytical characterizations. Intriguingly, in all cases, the nitro-substituted derivative exhibited a distinct behavior compared to the six other investigated derivatives, which was also addressed computationally. All seven new pentathiepines were crystallized, and their respective molecular structures were determined using single crystal X-ray diffraction. These structures are compared and discussed as are their respective packing patterns. Full article
(This article belongs to the Special Issue Synthesis and Properties of Heterocyclic Compounds: Recent Advances)
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Review

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18 pages, 1470 KiB  
Review
Recent Advances in the Synthesis of Rosettacin
by Xiao Tang, Yukang Jiang, Liangliang Song and Erik V. Van der Eycken
Molecules 2024, 29(10), 2176; https://doi.org/10.3390/molecules29102176 - 07 May 2024
Viewed by 63
Abstract
Camptothecin and its analogues show important antitumor activity and have been used in clinical studies. However, hydrolysis of lactone in the E ring seriously attenuates the antitumor activity. To change this situation, aromathecin alkaloids are investigated in order to replace camptothecins. Potential antitumor [...] Read more.
Camptothecin and its analogues show important antitumor activity and have been used in clinical studies. However, hydrolysis of lactone in the E ring seriously attenuates the antitumor activity. To change this situation, aromathecin alkaloids are investigated in order to replace camptothecins. Potential antitumor activity has obtained more and more attention from organic and pharmaceutical chemists. As a member of the aromathecin alkaloids, rosettacin has been synthesized via different methods. This review summarizes recent advances in the synthesis of rosettacin. Full article
(This article belongs to the Special Issue Synthesis and Properties of Heterocyclic Compounds: Recent Advances)
19 pages, 8433 KiB  
Review
Recent Trends in the Petasis Reaction: A Review of Novel Catalytic Synthetic Approaches with Applications of the Petasis Reaction
by Sadaf Saeed, Saba Munawar, Sajjad Ahmad, Asim Mansha, Ameer Fawad Zahoor, Ali Irfan, Ahmad Irfan, Katarzyna Kotwica-Mojzych, Malgorzata Soroka, Mariola Głowacka and Mariusz Mojzych
Molecules 2023, 28(24), 8032; https://doi.org/10.3390/molecules28248032 - 10 Dec 2023
Viewed by 1127
Abstract
The Petasis reaction, also called the Petasis Borono–Mannich reaction, is a multicomponent reaction that couples a carbonyl derivative, an amine and boronic acids to yield substituted amines. The reaction proceeds efficiently in the presence or absence of a specific catalyst and solvent. By [...] Read more.
The Petasis reaction, also called the Petasis Borono–Mannich reaction, is a multicomponent reaction that couples a carbonyl derivative, an amine and boronic acids to yield substituted amines. The reaction proceeds efficiently in the presence or absence of a specific catalyst and solvent. By employing this reaction, a diverse range of chiral derivatives can easily be obtained, including α-amino acids. A broad substrate scope, high yields, distinct functional group tolerance and the availability of diverse catalytic systems constitute key features of this reaction. In this review article, attention has been drawn toward the recently reported methodologies for executing the Petasis reaction to produce structurally simple to complex aryl/allyl amino scaffolds. Full article
(This article belongs to the Special Issue Synthesis and Properties of Heterocyclic Compounds: Recent Advances)
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