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Synthesis and Modification of Nitrogen Heterocyclic Compounds
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Synthesis and Modification of Nitrogen Heterocyclic Compounds

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

Deadline for manuscript submissions: closed (30 April 2023) | Viewed by 12346

Special Issue Editor

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

Special Issue Information

Dear Colleagues,

Nitrogen heterocyclic compounds are the core and foundation of chemical science and have always been at the forefront of the development of chemical science. This Special Issue aims to collect scientific papers focused on Synthesis and Modification of Nitrogen Heterocyclic Compounds. The most remarkable feature of nitrogen heterocyclic compounds is that it has strong creativity. It can not only create substances already existing in nature, but it can also create new substances with ideal properties and functions that do not exist in nature. Therefore, various methodologies, including cycloisomerization, cycloaddition, cross-coupling reaction, multicomponent condensation reactions, etc., are expected to develop to construct these basic skeletons.

Through the 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 Modification of Nitrogen Heterocyclic Compounds 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 the people.

Dr. Kai Sun
Guest Editor

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Keywords

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

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Published Papers (5 papers)

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Research

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19 pages, 6988 KiB  
Article
Ru-Controlled Thymine Tautomerization Frozen by a k1(O)-, k2(N,O)-Metallacycle: An Experimental and Theoretical Approach
by Silvia Bordoni, Riccardo Tarroni, Magda Monari, Stefano Cerini, Fabio Battaglia, Gabriele Micheletti, Carla Boga and Giacomo Drius
Molecules 2023, 28(10), 3983; https://doi.org/10.3390/molecules28103983 - 9 May 2023
Viewed by 1783
Abstract
The reaction of mer-(Ru(H)2(CO)(PPh3)3) (1) with one equivalent of thymine acetic acid (THAcH) unexpectedly produces the macrocyclic dimer k1(O), k2(N,O)-(Ru(CO)(PPh3)2THAc)2 (4) and, concomitantly, [...] Read more.
The reaction of mer-(Ru(H)2(CO)(PPh3)3) (1) with one equivalent of thymine acetic acid (THAcH) unexpectedly produces the macrocyclic dimer k1(O), k2(N,O)-(Ru(CO)(PPh3)2THAc)2 (4) and, concomitantly, the doubly coordinated species k1(O), k2(O,O)-(Ru(CO)(PPh3)2THAc) (5). The reaction promptly forms a complicated mixture of Ru-coordinated mononuclear species. With the aim of shedding some light in this context, two plausible reaction paths were proposed by attributing the isolated or spectroscopically intercepted intermediates on the basis of DFT-calculated energetic considerations. The cleavage of the sterically demanding equatorial phosphine in the mer-species releases enough energy to enable self-aggregation, producing the stable, symmetric 14-membered binuclear macrocycle of 4. The k1-acetate iminol (C=N-OH) unit of the mer-tautomer k1(O)-(Ru(CO)(PPh3)2(THAc)) (2) likely exhibits a stronger nucleophilic aptitude than the prevalent N(H)-C(O) amido species, thus accomplishing extra stabilization through concomitant k2(N,O)-thymine heteroleptic side-chelation. Furthermore, both the ESI-Ms and IR simulation spectra validated the related dimeric arrangement in solution, in agreement with the X-ray determination of the structure. The latter showed tautomerization to the iminol form. The 1H NMR spectra in chlorinated solvents of the kinetic mixture showed the simultaneous presence of 4 and the doubly coordinated 5, in rather similar amounts. THAcH added in excess preferentially reacts with 2 or trans-k2(O,O)-(RuH(CO)(PPh3)2THAc) (3) rather than attacking the starting Complex 1, promptly forming the species of 5. The proposed reaction paths were inferred by spectroscopically monitoring the intermediate species, for which the results were strongly dependent on the of conditions the reaction (stoichiometry, solvent polarity, time, and the concentration of the mixture). The selected mechanism proved to be more reliable, due to the final dimeric product stereochemistry. Full article
(This article belongs to the Special Issue Synthesis and Modification of Nitrogen Heterocyclic Compounds)
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13 pages, 9551 KiB  
Article
Visible Light-Induced Cascade Sulfonylation/Cyclization to Produce Quinoline-2,4-Diones under Metal-Free Conditions
by Yan Zhang, Ge Qiu, Fei Liu, Dongyang Zhao, Miao Tian and Kai Sun
Molecules 2023, 28(7), 3137; https://doi.org/10.3390/molecules28073137 - 31 Mar 2023
Cited by 3 | Viewed by 1791
Abstract
A general visible light-induced sulfonylation/cyclization to produce quinoline-2,4-diones was achieved under photocatalyst-free conditions. The reactions were performed at room temperature, and various substituents (halogen, alkyl, aryl) and substituted products were obtained with 29 examples within 2 h. Large-scale synthesis and derivatization study via [...] Read more.
A general visible light-induced sulfonylation/cyclization to produce quinoline-2,4-diones was achieved under photocatalyst-free conditions. The reactions were performed at room temperature, and various substituents (halogen, alkyl, aryl) and substituted products were obtained with 29 examples within 2 h. Large-scale synthesis and derivatization study via carbonyl reduction to produce easily modified hydroxyl groups and convenient N-Ts deprotection showed the potential utility of this strategy. Full article
(This article belongs to the Special Issue Synthesis and Modification of Nitrogen Heterocyclic Compounds)
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18 pages, 2639 KiB  
Article
One-Pot Synthesis of Isoxazole-Fused Tricyclic Quinazoline Alkaloid Derivatives via Intramolecular Cycloaddition of Propargyl-Substituted Methyl Azaarenes under Metal-Free Conditions
by Zhuo Wang, Yuhan Zhao, Jiaxin Chen, Mengyao Chen, Xuehan Li, Ting Jiang, Fang Liu, Xi Yang, Yuanyuan Sun and Yanping Zhu
Molecules 2023, 28(6), 2787; https://doi.org/10.3390/molecules28062787 - 20 Mar 2023
Cited by 2 | Viewed by 2402
Abstract
A practical method was developed for the convenient synthesis of isoxazole-fused tricyclic quinazoline alkaloids. This procedure accesses diverse isoxazole-fused tricyclic quinazoline alkaloids and their derivatives via intramolecular cycloaddition of methyl azaarenes with tert-butyl nitrite (TBN). In this method, TBN acts as the [...] Read more.
A practical method was developed for the convenient synthesis of isoxazole-fused tricyclic quinazoline alkaloids. This procedure accesses diverse isoxazole-fused tricyclic quinazoline alkaloids and their derivatives via intramolecular cycloaddition of methyl azaarenes with tert-butyl nitrite (TBN). In this method, TBN acts as the radical initiator and the source of N–O. Moreover, this protocol forms new C–N, C–C, and C–O bonds via sequence nitration and annulation in a one-pot process with broad substrate scope and functionalization of natural products. Full article
(This article belongs to the Special Issue Synthesis and Modification of Nitrogen Heterocyclic Compounds)
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8 pages, 1298 KiB  
Communication
A Facile Synthesis of 2-Oxazolines via Dehydrative Cyclization Promoted by Triflic Acid
by Tao Yang, Chengjie Huang, Jingyang Jia, Fan Wu and Feng Ni
Molecules 2022, 27(24), 9042; https://doi.org/10.3390/molecules27249042 - 19 Dec 2022
Cited by 3 | Viewed by 2421
Abstract
2-oxazolines are common moieties in numerous natural products, pharmaceuticals, and functional copolymers. Current methods for synthesizing 2-oxazolines mainly rely on stoichiometric dehydration agents or catalytic dehydration promoted by specific catalysts. These conditions either generate stoichiometric amounts of waste or require forcing azeotropic reflux [...] Read more.
2-oxazolines are common moieties in numerous natural products, pharmaceuticals, and functional copolymers. Current methods for synthesizing 2-oxazolines mainly rely on stoichiometric dehydration agents or catalytic dehydration promoted by specific catalysts. These conditions either generate stoichiometric amounts of waste or require forcing azeotropic reflux conditions. As such, a practical and robust method that promotes dehydrative cyclization while generating no byproducts would be attractive to oxazoline production. Herein, we report a triflic acid (TfOH)-promoted dehydrative cyclization of N-(2-hydroxyethyl)amides for synthesizing 2-oxazolines. This reaction tolerates various functional groups and generates water as the only byproduct. This method affords oxazoline with inversion of α-hydroxyl stereochemistry, suggesting that alcohol is activated as a leaving group under these conditions. Furthermore, the one-pot synthesis protocol of 2-oxazolines directly from carboxylic acids and amino alcohols is also provided. Full article
(This article belongs to the Special Issue Synthesis and Modification of Nitrogen Heterocyclic Compounds)
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Review

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35 pages, 6797 KiB  
Review
Synthesis and Application Dichalcogenides as Radical Reagents with Photochemical Technology
by Cairong Wang, Yan Zhang, Kai Sun, Tingting Yu, Fei Liu and Xin Wang
Molecules 2023, 28(4), 1998; https://doi.org/10.3390/molecules28041998 - 20 Feb 2023
Cited by 4 | Viewed by 2851
Abstract
Dichalcogenides (disulfides and diselenides), as reactants for organic transformations, are important and widely used because of their potential to react with nucleophiles, electrophilic reagents, and radical precursors. In recent years, in combination with photochemical technology, the application of dichalcogenides as stable radical reagents [...] Read more.
Dichalcogenides (disulfides and diselenides), as reactants for organic transformations, are important and widely used because of their potential to react with nucleophiles, electrophilic reagents, and radical precursors. In recent years, in combination with photochemical technology, the application of dichalcogenides as stable radical reagents has opened up a new route to the synthesis of various sulfur- and selenium-containing compounds. In this paper, synthetic strategies for disulfides and diselenides and their applications with photochemical technology are reviewed: (i) Cyclization of dichalcogenides with alkenes and alkynes; (ii) direct selenylation/sulfuration of C−H/C−C/C−N bonds; (iii) visible-light-enabled seleno- and sulfur-bifunctionalization of alkenes/alkynes; and (iv) Direct construction of the C(sp)–S bond. In addition, the scopes, limitations, and mechanisms of some reactions are also described. Full article
(This article belongs to the Special Issue Synthesis and Modification of Nitrogen Heterocyclic Compounds)
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