Polycyclic Heterocycles by Catalyzed Processes

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Catalysis in Organic and Polymer Chemistry".

Deadline for manuscript submissions: closed (31 December 2021) | Viewed by 11510

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Laboratory of Industrial and Synthetic Organic Chemistry (LISOC), Department of Chemistry and Chemical Technologies, University of Calabria, Via Pietro Bucci 12/C, 87036 Arcavacata di Rende, CS, Italy
Interests: innovative syntheses of high-value molecules through catalytic process; new syntheses of heterocyclic compounds of pharmaceutical interest; carbonylation catalyzed chemistry; application of unconventional solvents in advanced organic synthesis; synthesis of novel materials for advanced applications
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Special Issue Information

Polycyclic heterocycles are very important structural motifs existing in nature with significant agrochemical, biological, and pharmacological activities. The development of methods for the preparation of these polyheterocycles has been of longstanding interest. A quick and efficient synthetic route that leads to either natural products or functional materials is the aim of every organic protocol. However, it is essential to develop facile reactions that easily transfer simple building blocks into the desired complex structures in preferably few synthetic steps. Domino reactions represent a powerful strategy for the rapid formation of multiple bonds in one pot. In recent years, this class of reactions, involving metal-catalyzed bond activation, has emerged as an important field of research in organic synthesis.

This Special Issue’s scope is devoted to the latest advancements in the synthesis of polycyclic heterocyclic molecules. Both original research papers and reviews are welcomed. The scope is broad and may include the elaboration of new heterocyclization reactions or domino processes, catalyzed by homogeneous or heterogeneous catalysts, in conventional and/or nonconventional solvents for the synthesis of heterocycles of industrial, agrochemical, biological or pharmacological interest.

Submit your paper and select the Journal “Catalysts” and the Special Issue “Polycyclic Heterocycles by Catalyzed Processes” via: MDPI submission system. Please contact the Guest Editor or the journal editor (cicy.chen@mdpi.com) for any queries. Our papers will be published on a rolling basis and we will be pleased to receive your submission once you have finished it.

Dr. Raffaella Mancuso
Guest Editor

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Keywords

  • cyclization reaction
  • catalyzed organic synthesis
  • domino reaction
  • heterogeneous catalysis
  • heterocycles
  • heterocyclization reaction
  • homogeneous catalysis
  • polycyclic heterocycles
  • polyheterocycles

Published Papers (4 papers)

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Research

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18 pages, 12744 KiB  
Article
A Stereoselective, Multicomponent Catalytic Carbonylative Approach to a New Class of α,β-Unsaturated γ-Lactam Derivatives
by Raffaella Mancuso, Ida Ziccarelli, Matteo Brindisi, Cosimo D. Altomare, Luca Frattaruolo, Aurelia Falcicchio, Nicola Della Ca’, Anna Rita Cappello and Bartolo Gabriele
Catalysts 2021, 11(2), 227; https://doi.org/10.3390/catal11020227 - 09 Feb 2021
Cited by 13 | Viewed by 2541
Abstract
We report a stereoselective, multicomponent catalytic carbonylative approach to a new class of α,β-unsaturated γ-lactam derivatives with potential biological activity, that are, alkyl (Z)-2-(2-oxopyrrolidin-3-ylidene)acetates. Our method is based on the catalytic assembly of readily available building blocks, namely, homopropargylic amines, carbon [...] Read more.
We report a stereoselective, multicomponent catalytic carbonylative approach to a new class of α,β-unsaturated γ-lactam derivatives with potential biological activity, that are, alkyl (Z)-2-(2-oxopyrrolidin-3-ylidene)acetates. Our method is based on the catalytic assembly of readily available building blocks, namely, homopropargylic amines, carbon monoxide, an alcohol, and oxygen (from air). These simple substrates are efficiently activated in ordered sequence under the action of a very simple catalytic system, consisting of PdI2 in conjunction with KI to give the γ-lactam products in 47–85% yields. Carbonylation reactions are carried out at 100 °C for 2–5 h under 40 atm of a 4:1 mixture of CO‒air, with 0.5–5 mol% of PdI2 and 5–50 mol% of KI. Full article
(This article belongs to the Special Issue Polycyclic Heterocycles by Catalyzed Processes)
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24 pages, 5685 KiB  
Article
Versatile Coordination Polymer Catalyst for Acid Reactions Involving Biobased Heterocyclic Chemicals
by Margarida M. Antunes, Ricardo F. Mendes, Filipe A. Almeida Paz and Anabela A. Valente
Catalysts 2021, 11(2), 190; https://doi.org/10.3390/catal11020190 - 01 Feb 2021
Cited by 8 | Viewed by 3022
Abstract
The chemical valorization/repurposing of biomass-derived chemicals contributes to a biobased economy. Furfural (Fur) is a recognized platform chemical produced from renewable lignocellulosic biomass, and furfuryl alcohol (FA) is its most important application. The aromatic aldehydes Fur and benzaldehyde (Bza) are commonly found in [...] Read more.
The chemical valorization/repurposing of biomass-derived chemicals contributes to a biobased economy. Furfural (Fur) is a recognized platform chemical produced from renewable lignocellulosic biomass, and furfuryl alcohol (FA) is its most important application. The aromatic aldehydes Fur and benzaldehyde (Bza) are commonly found in the slate of compounds produced via biomass pyrolysis. On the other hand, glycerol (Gly) is a by-product of the industrial production of biodiesel, derived from fatty acid components of biomass. This work focuses on acid catalyzed routes of Fur, Bza, Gly and FA, using a versatile crystalline lamellar coordination polymer catalyst, namely [Gd(H4nmp)(H2O)2]Cl·2H2O (1) [H6nmp=nitrilotris(methylenephosphonic acid)] synthesized via an ecofriendly, relatively fast, mild microwave-assisted approach (in water, 70 °C/40 min). This is the first among crystalline coordination polymers or metal-organic framework type materials studied for the Fur/Gly and Bza/Gly reactions, giving heterobicyclic products of the type dioxolane and dioxane, and was also effective for the FA/ethanol reaction. 1 was stable and promoted the target catalytic reactions, selectively leading to heterobicyclic dioxane and dioxolane type products in the Fur/Gly and Bza/Gly reactions (up to 91% and 95% total yields respectively, at 90 °C/4 h), and, on the other hand, 2-(ethoxymethyl)furan and ethyl levulinate from heterocyclic FA. Full article
(This article belongs to the Special Issue Polycyclic Heterocycles by Catalyzed Processes)
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17 pages, 5787 KiB  
Article
2-Aminobenzothiazole-Containing Copper(II) Complex as Catalyst in Click Chemistry: An Experimental and Theoretical Study
by Lahoucine Bahsis, Meryem Hrimla, Hicham Ben El Ayouchia, Hafid Anane, Miguel Julve and Salah-Eddine Stiriba
Catalysts 2020, 10(7), 776; https://doi.org/10.3390/catal10070776 - 11 Jul 2020
Cited by 8 | Viewed by 2539
Abstract
The reaction of copper(II) acetate with the 2-aminobenzothiazole (abt) heterocycle affords the new copper(II) complex of formula [Cu(abt)2(OOCCH3)2] (1) in a straightforward manner. Compound 1 served as a precatalyst for azide/alkyne cycloaddition reactions (CuAAC) in [...] Read more.
The reaction of copper(II) acetate with the 2-aminobenzothiazole (abt) heterocycle affords the new copper(II) complex of formula [Cu(abt)2(OOCCH3)2] (1) in a straightforward manner. Compound 1 served as a precatalyst for azide/alkyne cycloaddition reactions (CuAAC) in water, leading to 1,4-disubstituted-1,2,3-triazole derivatives in a regioselective manner and with excellent yields at room temperature. The main advantages of the coordination of such a heterocyclic ligand in 1 are its strong σ-donating ability (N-Cu), nontoxicity and biological properties. In addition, the click chemistry reaction conditions using 1 allow the formation of a great variety of 1,2,3-triazole-based heterocyclic compounds that make this protocol potentially relevant from biological and sustainable viewpoints. A molecular electron density theory (MEDT) study was performed by using density functional theory (DFT) calculations at the B3LYP/6-31G(d,p) (LANL2DZ for Cu) level to understand the observed regioselectivity in the CuAAC reaction. The intramolecular nature of this reaction accounts for the regioselective formation of the 1,4-regioisomeric triazole derivatives. The ionic nature of the starting copper-acetylide precludes any type of covalent interaction throughout the reaction, as supported by the electron localization function (ELF) topological analysis, reaffirming the zwitterionic-type (zw-type) mechanism of the copper(I)/aminobenzothiazole-catalysed azide-alkyne cycloaddition reactions. Full article
(This article belongs to the Special Issue Polycyclic Heterocycles by Catalyzed Processes)
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Review

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14 pages, 3370 KiB  
Review
Copper-Catalyzed Synthesis of Coumarins. A Mini-Review
by Renato Dalpozzo and Raffaella Mancuso
Catalysts 2021, 11(11), 1382; https://doi.org/10.3390/catal11111382 - 16 Nov 2021
Cited by 4 | Viewed by 2611
Abstract
Coumarin (2H-chromen-2-one) derivatives have important uses in medicinal and synthetic chemistry, for example, as fluorescent probes. These properties have prompted chemists to develop efficient synthetic methods to synthesize the coumarin core and/or to functionalize it. In this context, many metal-catalyzed syntheses [...] Read more.
Coumarin (2H-chromen-2-one) derivatives have important uses in medicinal and synthetic chemistry, for example, as fluorescent probes. These properties have prompted chemists to develop efficient synthetic methods to synthesize the coumarin core and/or to functionalize it. In this context, many metal-catalyzed syntheses of coumarins have been introduced; among them, copper-catalyzed reactions appear to be very promising owing to the non-toxicity and cheapness of copper complexes. In this mini-review, the results in this field are summarized. We hope to stimulate other applications of these complexes in the preparation of coumarin derivatives. Full article
(This article belongs to the Special Issue Polycyclic Heterocycles by Catalyzed Processes)
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