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Molecules
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Preparation of Heterocycles by Metal-Promoted Reactions
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Preparation of Heterocycles by Metal-Promoted Reactions

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

Deadline for manuscript submissions: closed (31 August 2021) | Viewed by 12211

Special Issue Editors

Dr. Julien Petrignet

E-Mail Website
Guest Editor
Laboratoire Synthèse et Isolement de Molécules Bioactives (SIMBA, EA 7502), Université de Tours, Faculté de Pharmacie, Parc de Grandmont, 31 Avenue Monge, 37200 Tours, France
Interests: methodology in organic synthesis; catalysis by copper complexes; palladocatalysed reactions; heterocycles; medicinal chemistry
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Mauro Pineschi

E-Mail Website
Guest Editor
Department of Pharmacy, University of Pisa, Pisa, Italy
Interests: synthetic methodologies; asymmetric synthesis; sustainable synthesis; copper catalysis; strained heterocycles; synthesis of heterocyclic scaffolds of medicinal interest

Special Issue Information

Dear Colleagues,

The importance of heterocycles in the field of natural compounds and fine chemistry is well established. The diversity of heterocycles is substantial due to the many possible combinations between the nature of the heteroatom(s) (N, O, S, etc.) and of the cycle(s) (size; fused systems, etc.), just as much as the synthetic approaches for the construction of these scaffolds. This Special Issue is devoted to the latest research that is ongoing on the heterocyclic synthesis and their functionalization involving a metal-promoted step. Contributions (communications, full papers and reviews) that discuss innovative methodologies involving a metal (transition-metal or not, catalyzed or stoichiometric approaches) around known heterocyclic or poly-heterocyclic scaffolds as well as new structures are welcome.

Dr. Julien Petrignet
Prof. Dr. Mauro Pineschi
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

  • Organic synthesis
  • Heterocyclic chemistry
  • Metal-promoted reactions
  • Cross-coupling reactions
  • Catalysis
  • Domino-reactions
  • Stoichiometric approaches
  • Single heterocycles
  • Fused heterocycles
  • Enantioselective catalysis

Published Papers (4 papers)

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Research

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22 pages, 2008 KiB  
Article
Synthesis of New Highly Functionalized 1H-Indole-2-carbonitriles via Cross-Coupling Reactions
by Asma Hrizi, Manon Cailler, Moufida Romdhani-Younes, Yvan Carcenac and Jérôme Thibonnet
Molecules 2021, 26(17), 5287; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26175287 - 31 Aug 2021
Cited by 1 | Viewed by 2638
Abstract
An approach for the preparation of polysubstituted indole-2-carbonitriles through a cross-coupling reaction of compounds 1-(but-2-ynyl)-1H-indole-2-carbonitriles and 1-benzyl-3-iodo-1H-indole-2-carbonitriles is described. The reactivity of indole derivatives with iodine at position 3 was studied using cross-coupling reactions. The Sonogashira, Suzuki–Miyaura, Stille and [...] Read more.
An approach for the preparation of polysubstituted indole-2-carbonitriles through a cross-coupling reaction of compounds 1-(but-2-ynyl)-1H-indole-2-carbonitriles and 1-benzyl-3-iodo-1H-indole-2-carbonitriles is described. The reactivity of indole derivatives with iodine at position 3 was studied using cross-coupling reactions. The Sonogashira, Suzuki–Miyaura, Stille and Heck cross-couplings afforded a variety of di-, tri- and tetra-substituted indole-2-carbonitriles. Full article
(This article belongs to the Special Issue Preparation of Heterocycles by Metal-Promoted Reactions)
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9 pages, 897 KiB  
Article
Synthesis of 2-Substitued Indoles via Pd-Catalysed Cyclization in an Aqueous Micellar Medium
by Sofia Siciliano, Elena Cini, Maurizio Taddei and Giorgia Vinciarelli
Molecules 2021, 26(13), 3917; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26133917 - 26 Jun 2021
Cited by 7 | Viewed by 2245
Abstract
The synthesis of 2-substituted indoles starting from the corresponding unprotected 2-alkynylanilines was made possible in 3% TPGS-750-M water using Pd(OAc)2 alone as the catalyst. The reaction was sensitive to the heating mode respect to the nature of the starting material as, in [...] Read more.
The synthesis of 2-substituted indoles starting from the corresponding unprotected 2-alkynylanilines was made possible in 3% TPGS-750-M water using Pd(OAc)2 alone as the catalyst. The reaction was sensitive to the heating mode respect to the nature of the starting material as, in many cases, convectional heating was better than microwave dielectric heating. The MW (microwave) delivery mode had also an influence in the formation of by-products and, consequently, product yields. A tandem Sonogashira-cyclisation reaction was also accomplished using Pd(OAc)2/Xphos in the nanomicellar water environment. Full article
(This article belongs to the Special Issue Preparation of Heterocycles by Metal-Promoted Reactions)
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16 pages, 3307 KiB  
Article
Selective Synthesis of N-Acylnortropane Derivatives in Palladium-Catalysed Aminocarbonylation
by László Kollár, Ádám Erdélyi, Haroon Rasheed and Attila Takács
Molecules 2021, 26(6), 1813; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26061813 - 23 Mar 2021
Cited by 4 | Viewed by 2448
Abstract
The aminocarbonylation of various alkenyl and (hetero)aryl iodides was carried out using tropane-based amines of biological importance, such as 8-azabicyclo[3.2.1]octan-3-one (nortropinone) and 3α-hydroxy-8-azabicyclo[3.2.1]octane (nortropine) as N-nucleophile. Using iodoalkenes, the two nucleophiles were selectively converted to the corresponding amide in the presence of [...] Read more.
The aminocarbonylation of various alkenyl and (hetero)aryl iodides was carried out using tropane-based amines of biological importance, such as 8-azabicyclo[3.2.1]octan-3-one (nortropinone) and 3α-hydroxy-8-azabicyclo[3.2.1]octane (nortropine) as N-nucleophile. Using iodoalkenes, the two nucleophiles were selectively converted to the corresponding amide in the presence of Pd(OAc)2/2 PPh3 catalysts. In the presence of several iodo(hetero)arenes, the application of the bidentate Xantphos was necessary to produce the target compounds selectively. The new carboxamides of varied structure, formed in palladium-catalyzed aminocarbonylation reactions, were isolated and fully characterized. In this way, a novel synthetic method has been developed for the producing of N-acylnortropane derivatives of biological importance. Full article
(This article belongs to the Special Issue Preparation of Heterocycles by Metal-Promoted Reactions)
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Review

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38 pages, 19094 KiB  
Review
Metal-Promoted Heterocyclization: A Heterosynthetic Approach to Face a Pandemic Crisis
by Federico Vittorio Rossi, Dario Gentili and Enrico Marcantoni
Molecules 2021, 26(9), 2620; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26092620 - 29 Apr 2021
Cited by 2 | Viewed by 4263
Abstract
The outbreak of SARS-CoV-2 has drastically changed our everyday life and the life of scientists from all over the world. In the last year, the scientific community has faced this worldwide threat using any tool available in order to find an effective response. [...] Read more.
The outbreak of SARS-CoV-2 has drastically changed our everyday life and the life of scientists from all over the world. In the last year, the scientific community has faced this worldwide threat using any tool available in order to find an effective response. The recent formulation, production, and ongoing administration of vaccines represent a starting point in the battle against SARS-CoV-2, but they cannot be the only aid available. In this regard, the use of drugs capable to mitigate and fight the virus is a crucial aspect of the pharmacological strategy. Among the plethora of approved drugs, a consistent element is a heterocyclic framework inside its skeleton. Heterocycles have played a pivotal role for decades in the pharmaceutical industry due to their high bioactivity derived from anticancer, antiviral, and anti-inflammatory capabilities. In this context, the development of new performing and sustainable synthetic strategies to obtain heterocyclic molecules has become a key focus of scientists. In this review, we present the recent trends in metal-promoted heterocyclization, and we focus our attention on the construction of heterocycles associated with the skeleton of drugs targeting SARS-CoV-2 coronavirus. Full article
(This article belongs to the Special Issue Preparation of Heterocycles by Metal-Promoted Reactions)
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