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Recent Advances in Heterocycles Synthesis
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Recent Advances in Heterocycles Synthesis

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

Deadline for manuscript submissions: closed (30 September 2023) | Viewed by 16188

Special Issue Editors

Prof. Dr. Renzo Luisi

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Guest Editor
FLAME-Lab, Flow Chemistry, and Microreactor Technology Laboratory, Department of Pharmacy - Drug Sciences, University of Bari "A. Moro", Via E. Orabona 4, 70125 Bari, Italy
Interests: organic synthesis; flow chemistry; chemistry of strained heterocycles; green chemistry; fluorine chemistry
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Leonardo Degennaro

E-Mail Website
Guest Editor
FLAME-Lab, Flow Chemistry, and Microreactor Technology Laboratory, Department of Pharmacy - Drug Sciences, University of Bari "A. Moro", Via E. Orabona 4, 70125 Bari, Italy
Interests: organic synthesis; flow chemistry; chemistry of strained heterocycles; green chemistry; fluorine chemistry
Dr. Marco Colella

E-Mail Website
Guest Editor
FLAME-Lab, Flow Chemistry, and Microreactor Technology Laboratory, Department of Pharmacy - Drug Sciences, University of Bari "A. Moro", Via E. Orabona 4, 70125 Bari, Italy
Interests: organic synthesis; flow chemistry; chemistry of strained heterocycles; green chemistry; fluorine chemistry

Special Issue Information

Dear Colleagues,

Heterocyclic compounds are of pivotal importance and pervasive in several areas of our daily life. From medicines to smart materials, and from natural products to foodstuffs, heterocycles are essential cores in a countless number of useful molecules. This is the reason, since the beginning of the 19th century, interest towards the chemistry of heterocycles never ended. Synthetic chemists continue to develop accurate and selective tactics to accessing heterocyclic scaffolds. In the last decade, progress in catalysis, photo- and electrocatalysis, and progress in synthetic technologies boosted the development of efficient methods to prepare heterocycles. New chemical space has been explored, and new functionalized heterocycles have been prepared. At the same time, new functions and biological activities have been discovered. This Special Issue aims at providing a useful resource of knowledge on recent achievements in the field of heterocyclic chemistry, and we warmly invite colleagues to contribute to this Special Issue with both experimental and theoretical contributions in order to expand our knowledge in this endless research area. Original experimental and computational studies are welcome as well as critical analyses of existing and future challenges in the field.

Prof. Dr. Renzo Luisi
Prof. Dr. Leonardo Degennaro
Dr. Marco Colella
Guest Editors

Manuscript Submission Information

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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

  • heterocyclic synthesis
  • saturated heterocycles
  • aromatic heterocycles
  • strained heterocycles
  • catalytic methods
  • photochemical methods
  • electrochemical methods
  • computational methods
  • asymmetric synthesis
  • natural products
  • heterocycles in medicinal chemistry
  • heterocycles in material science

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Published Papers (6 papers)

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Research

15 pages, 1865 KiB  
Article
Synthesis of Novel Benzo[b][1,6]naphthyridine Derivatives and Investigation of Their Potential as Scaffolds of MAO Inhibitors
by Larisa N. Kulikova, Ghulam Reza Raesi, Daria D. Levickaya, Rosa Purgatorio, Gabriella La Spada, Marco Catto, Cosimo D. Altomare and Leonid G. Voskressensky
Molecules 2023, 28(4), 1662; https://doi.org/10.3390/molecules28041662 - 9 Feb 2023
Cited by 4 | Viewed by 2085
Abstract
In this work, 2-alkyl-10-chloro-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridines were obtained and their reactivity was studied. Novel derivatives of the tricyclic scaffold, including 1-phenylethynyl (5), 1-indol-3-yl (8), and azocino[4,5-b]quinoline (10) derivatives, were synthesized and characterized herein for the [...] Read more.
In this work, 2-alkyl-10-chloro-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridines were obtained and their reactivity was studied. Novel derivatives of the tricyclic scaffold, including 1-phenylethynyl (5), 1-indol-3-yl (8), and azocino[4,5-b]quinoline (10) derivatives, were synthesized and characterized herein for the first time. Among the newly synthesized derivatives, 5c–h proved to be MAO B inhibitors with potency in the low micromolar range. In particular, the 1-(2-(4-fluorophenyl)ethynyl) analog 5g achieved an IC50 of 1.35 μM, a value close to that of the well-known MAO B inhibitor pargyline. Full article
(This article belongs to the Special Issue Recent Advances in Heterocycles Synthesis)
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30 pages, 1746 KiB  
Article
Synthesis of New Azetidine and Oxetane Amino Acid Derivatives through Aza-Michael Addition of NH-Heterocycles with Methyl 2-(Azetidin- or Oxetan-3-Ylidene)Acetates
by Emilis Gudelis, Sonata Krikštolaitytė, Monika Stančiauskaitė, Urtė Šachlevičiūtė, Aurimas Bieliauskas, Vaida Milišiūnaitė, Rokas Jankauskas, Neringa Kleizienė, Frank A. Sløk and Algirdas Šačkus
Molecules 2023, 28(3), 1091; https://doi.org/10.3390/molecules28031091 - 21 Jan 2023
Cited by 5 | Viewed by 3739
Abstract
In this paper, a simple and efficient synthetic route for the preparation of new heterocyclic amino acid derivatives containing azetidine and oxetane rings was described. The starting (N-Boc-azetidin-3-ylidene)acetate was obtained from (N-Boc)azetidin-3-one by the DBU-catalysed Horner–Wadsworth–Emmons reaction, followed by [...] Read more.
In this paper, a simple and efficient synthetic route for the preparation of new heterocyclic amino acid derivatives containing azetidine and oxetane rings was described. The starting (N-Boc-azetidin-3-ylidene)acetate was obtained from (N-Boc)azetidin-3-one by the DBU-catalysed Horner–Wadsworth–Emmons reaction, followed by aza-Michael addition with NH-heterocycles to yield the target functionalised 3-substituted 3-(acetoxymethyl)azetidines. Methyl 2-(oxetan-3-ylidene)acetate was obtained in a similar manner, which was further treated with various (N-Boc-cycloaminyl)amines to yield the target 3-substituted 3-(acetoxymethyl)oxetane compounds. The synthesis and diversification of novel heterocyclic amino acid derivatives were achieved through the Suzuki–Miyaura cross-coupling from the corresponding brominated pyrazole–azetidine hybrid with boronic acids. The structures of the novel heterocyclic compounds were confirmed via 1H-, 13C-, 15N-, and 19F-NMR spectroscopy, as well as HRMS investigations. Full article
(This article belongs to the Special Issue Recent Advances in Heterocycles Synthesis)
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18 pages, 1767 KiB  
Article
Synthesis of 2-Cyanobenzothiazoles via Pd-Catalyzed/Cu-Assisted C-H Functionalization/Intramolecular C-S Bond Formation from N-Arylcyanothioformamides
by Nathan Broudic, Alexandra Pacheco-Benichou, Corinne Fruit and Thierry Besson
Molecules 2022, 27(23), 8426; https://doi.org/10.3390/molecules27238426 - 1 Dec 2022
Cited by 5 | Viewed by 2310
Abstract
We report herein on a catalytic system involving palladium and copper to achieve the cyclization of N-arylcyanothioformamides and the synthesis of 2-cyanobenzothiazoles. The C-H functionalization/intramolecular C-S bond formation reaction was achieved in the presence of air, using 2.0 equiv of an inorganic [...] Read more.
We report herein on a catalytic system involving palladium and copper to achieve the cyclization of N-arylcyanothioformamides and the synthesis of 2-cyanobenzothiazoles. The C-H functionalization/intramolecular C-S bond formation reaction was achieved in the presence of air, using 2.0 equiv of an inorganic additive (KI). In many cases, the reaction led to a sole product regioselectively obtained in good yields, allowing the synthesis of a wide range of substituted 2-cyanobenzothiazole derivatives, providing valuable building blocks for the design of more complex heterocyclic or molecular labeling systems. Full article
(This article belongs to the Special Issue Recent Advances in Heterocycles Synthesis)
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13 pages, 2197 KiB  
Article
Synthesis of Isomeric 3-Benzazecines Decorated with Endocyclic Allene Moiety and Exocyclic Conjugated Double Bond and Evaluation of Their Anticholinesterase Activity
by Alexander A. Titov, Rosa Purgatorio, Arina Y. Obydennik, Anna V. Listratova, Tatiana N. Borisova, Modesto de Candia, Marco Catto, Cosimo D. Altomare, Alexey V. Varlamov and Leonid G. Voskressensky
Molecules 2022, 27(19), 6276; https://doi.org/10.3390/molecules27196276 - 23 Sep 2022
Cited by 7 | Viewed by 1855
Abstract
Transformations of 1-methoxymethylethynyl substituted isoquinolines triggered by terminal alkynes in alcohols were studied and new 3-benzazecine-containing compounds synthesized, such as 6-methoxymethyl-3-benzazecines incorporating an endocyclic C6–C8 allene fragment and the -ylidene derivatives 6-methoxymethylene-3-benzazecines. The reaction mechanisms were investigated and a preliminary in vitro screening [...] Read more.
Transformations of 1-methoxymethylethynyl substituted isoquinolines triggered by terminal alkynes in alcohols were studied and new 3-benzazecine-containing compounds synthesized, such as 6-methoxymethyl-3-benzazecines incorporating an endocyclic C6–C8 allene fragment and the -ylidene derivatives 6-methoxymethylene-3-benzazecines. The reaction mechanisms were investigated and a preliminary in vitro screening of their potential inhibitory activities against human acetyl- and butyrylcholinesterases (AChE and BChE) and monoamine oxidases A and B (MAO-A and MAO-B) showed that the allene compounds were more potent than the corresponding -ylidene ones as selective AChE inhibitors. Among the allenes, 3e (R3 = CH2OMe) was found to be a competitive AChE inhibitor with a low micromolar inhibition constant value (Ki = 4.9 μM), equipotent with the corresponding 6-phenyl derivative 3n (R3 = Ph, Ki = 4.5 μM), but 90-fold more water-soluble. Full article
(This article belongs to the Special Issue Recent Advances in Heterocycles Synthesis)
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Graphical abstract

32 pages, 2333 KiB  
Article
Synthesis and Characterization of Novel Heterocyclic Chalcones from 1-Phenyl-1H-pyrazol-3-ol
by Arminas Urbonavičius, Graziana Fortunato, Emilija Ambrazaitytė, Elena Plytninkienė, Aurimas Bieliauskas, Vaida Milišiūnaitė, Renzo Luisi, Eglė Arbačiauskienė, Sonata Krikštolaitytė and Algirdas Šačkus
Molecules 2022, 27(12), 3752; https://doi.org/10.3390/molecules27123752 - 10 Jun 2022
Cited by 10 | Viewed by 3451
Abstract
An efficient synthetic route to construct diverse pyrazole-based chalcones from 1-phenyl-1H-pyrazol-3-ols bearing a formyl or acetyl group on the C4 position of pyrazole ring, employing a base-catalysed Claisen–Schmidt condensation reaction, is described. Isomeric chalcones were further reacted with N-hydroxy-4-toluenesulfonamide and [...] Read more.
An efficient synthetic route to construct diverse pyrazole-based chalcones from 1-phenyl-1H-pyrazol-3-ols bearing a formyl or acetyl group on the C4 position of pyrazole ring, employing a base-catalysed Claisen–Schmidt condensation reaction, is described. Isomeric chalcones were further reacted with N-hydroxy-4-toluenesulfonamide and regioselective formation of 3,5-disubstituted 1,2-oxazoles was established. The novel pyrazole-chalcones and 1,2-oxazoles were characterized by an in-depth analysis of NMR spectral data, which were obtained through a combination of standard and advanced NMR spectroscopy techniques. Full article
(This article belongs to the Special Issue Recent Advances in Heterocycles Synthesis)
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13 pages, 2895 KiB  
Article
Dynamic Phenomena and Complexation Effects in the α-Lithiation and Asymmetric Functionalization of Azetidines
by Pantaleo Musci, Marco Colella, Angela Altomare, Giuseppe Romanazzi, Nadeem S. Sheikh, Leonardo Degennaro and Renzo Luisi
Molecules 2022, 27(9), 2847; https://doi.org/10.3390/molecules27092847 - 29 Apr 2022
Cited by 5 | Viewed by 1814
Abstract
In this work it is demonstrated that enantiomerically enriched N-alkyl 2-oxazolinylazetidines undergo exclusive α-lithiation, and that the resulting lithiated intermediate is chemically stable but configurationally labile under the given experimental conditions that afford enantioenriched N-alkyl-2,2-disubstituted azetidines. Although this study reveals the [...] Read more.
In this work it is demonstrated that enantiomerically enriched N-alkyl 2-oxazolinylazetidines undergo exclusive α-lithiation, and that the resulting lithiated intermediate is chemically stable but configurationally labile under the given experimental conditions that afford enantioenriched N-alkyl-2,2-disubstituted azetidines. Although this study reveals the configurational instability of the diastereomeric lithiated azetidines, it points out an interesting stereoconvergence of such lithiated intermediates towards the thermodynamically stable species, making the overall process highly stereoselective (er > 95:5, dr > 85:15) after trapping with electrophiles. This peculiar behavior has been rationalized by considering the dynamics at the azetidine nitrogen atom, the inversion at the C-Li center supported by in situ FT-IR experiments, and DFT calculations that suggested the presence of η3-coordinated species for diastereomeric lithiated azetidines. The described situation contrasted with the demonstrated stability of the smaller lithiated aziridine analogue. The capability of oxazolinylazetidines to undergo different reaction patterns with organolithium bases supports the model termed “dynamic control of reactivity” of relevance in organolithium chemistry. It has been demonstrated that only 2,2-substituted oxazolinylazetidines with suitable stereochemical requirements could undergo C=N addition of organolithiums in non-coordinating solvents, leading to useful precursors of chiral (er > 95:5) ketoazetidines. Full article
(This article belongs to the Special Issue Recent Advances in Heterocycles Synthesis)
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