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Molecules
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Synthesis and Functionalization of Nitrogen Heterocycles
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Synthesis and Functionalization of Nitrogen Heterocycles

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

Deadline for manuscript submissions: closed (28 February 2025) | Viewed by 2704

Special Issue Editors

Dr. Kai Sun

E-Mail Website
Guest Editor
College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China
Interests: heterocyclic chemical; amination; radical chemical; photochemical synthesis; C-H bond functionalization; cascade cyclization
Special Issues, Collections and Topics in MDPI journals
Dr. Qilin Wang

E-Mail Website
Guest Editor
College of Chemistry and Molecular Sciences, Henan University, Kaifeng 475004, China
Interests: acid- or base-catalyzed cascade cyclization; construction of bridged- or spiroheterocycles; asymmetric catalysis and synthesis

Special Issue Information

Dear Colleagues,

Nitrogenous compounds hold a privileged position in the preparation of drugs, agrochemicals, polymers and other functional materials. In particular, nitrogen species are presented in more than 80% of the top 200 pharmaceuticals, and two thirds of these N-containing medicines contain N-heterocyclic skeletons. Therefore, the development of different synthetic methods for N-heterocycles has attracted great endeavor in organic synthetic chemistry. To date, various methodologies, including cycloisomerization, cycloaddition, cross-coupling reaction and multicomponent condensation reactions, etc., have been developed to construct these basic skeletons.

Through intersection and integration with other disciplines, nitrogen heterocyclic chemistry has produced many new interdisciplinary and cutting-edge fields, and also provides new opportunities for its development. Therefore, the significance of this Special Issue for the synthesis and functionalization of nitrogen heterocycles is not only on paper, but also further invested in the great cause of national production and building socialism, which is beneficial to the country and people.

Dr. Kai Sun
Dr. Qilin 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

  • nitrogen heterocycles
  • C-H bond functionalization
  • cascade cyclization
  • multi-component reaction
  • cycloaddition
  • radical chemistry

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Published Papers (2 papers)

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Research

19 pages, 1820 KiB  
Article
Synthesis of Functionalized 1H-Imidazoles via Denitrogenative Transformation of 5-Amino-1,2,3-Triazoles
by Pavel S. Gribanov, Anna N. Philippova, Alexander F. Smol’yakov, Diana N. Tukhvatullina, Viktoria A. Vlasova, Maxim A. Topchiy, Andrey F. Asachenko and Sergey N. Osipov
Molecules 2025, 30(7), 1401; https://doi.org/10.3390/molecules30071401 - 21 Mar 2025
Viewed by 1068
Abstract
An efficient access to novel 2-substituted 1H-imidazole derivatives was developed based on acid-mediated denitrogenative transformation of 5-amino-1,2,3-triazole derivatives available through dipolar azide−nitrile cycloaddition (DCR). The proposed approach includes intramolecular cyclization of 5-amino-4-aryl-1-(2,2-diethoxyethyl) 1,2,3-triazoles followed by triazole ring opening and insertion of [...] Read more.
An efficient access to novel 2-substituted 1H-imidazole derivatives was developed based on acid-mediated denitrogenative transformation of 5-amino-1,2,3-triazole derivatives available through dipolar azide−nitrile cycloaddition (DCR). The proposed approach includes intramolecular cyclization of 5-amino-4-aryl-1-(2,2-diethoxyethyl) 1,2,3-triazoles followed by triazole ring opening and insertion of in situ formed carbene intermediate into the O-H bond of different alcohols under acidic conditions. Full article
(This article belongs to the Special Issue Synthesis and Functionalization of Nitrogen Heterocycles)
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16 pages, 6630 KiB  
Article
Regioselective Nucleophilic Aromatic Substitution: Theoretical and Experimental Insights into 4-Aminoquinazoline Synthesis as a Privileged Structure in Medicinal Chemistry
by Maria Letícia de Castro Barbosa, Pedro de Sena Murteira Pinheiro, Raissa Alves da Conceição, José Ricardo Pires, Lucas Silva Franco, Carlos Mauricio R. Sant’Anna, Eliezer J. Barreiro and Lídia Moreira Lima
Molecules 2024, 29(24), 6021; https://doi.org/10.3390/molecules29246021 - 20 Dec 2024
Viewed by 1308
Abstract
The 4-aminoquinazoline scaffold is a privileged structure in medicinal chemistry. Regioselective nucleophilic aromatic substitution (SNAr) for replacing the chlorine atom at the 4-position of 2,4-dichloroquinazoline precursors is well documented in the scientific literature and has proven useful in synthesizing 2-chloro-4-aminoquinazolines and/or [...] Read more.
The 4-aminoquinazoline scaffold is a privileged structure in medicinal chemistry. Regioselective nucleophilic aromatic substitution (SNAr) for replacing the chlorine atom at the 4-position of 2,4-dichloroquinazoline precursors is well documented in the scientific literature and has proven useful in synthesizing 2-chloro-4-aminoquinazolines and/or 2,4-diaminoquinazolines for various therapeutic applications. While numerous reports describe reaction conditions involving different nucleophiles, solvents, temperatures, and reaction times, discussions on the regioselectivity of the SNAr step remain scarce. In this study, we combined DFT calculations with 2D-NMR analysis to characterize the structure and understand the electronic factors underlying the regioselective SNAr of 2,4-dichloroquinazolines for the synthesis of bioactive 4-aminoquinazolines. DFT calculations revealed that the carbon atom at the 4-position of 2,4-dichloroquinazoline has a higher LUMO coefficient, making it more susceptible to nucleophilic attack. This observation aligns with the calculated lower activation energy for nucleophilic attack at this position, supporting the regioselectivity of the reaction. To provide guidance for the structural confirmation of 4-amino-substituted product formation when multiple regioisomers are possible, we employed 2D-NMR methods to verify the 4-position substitution pattern in synthesized bioactive 2-chloro-4-aminoquinazolines. These findings are valuable for future research, as many synthetic reports assume regioselective outcomes without sufficient experimental verification. Full article
(This article belongs to the Special Issue Synthesis and Functionalization of Nitrogen Heterocycles)
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