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Advances on the Application of N-O Bond Compounds
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Advances on the Application of N-O Bond Compounds

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

Deadline for manuscript submissions: closed (31 October 2023) | Viewed by 20743

Special Issue Editors

Prof. Dr. Dongliang Mo

E-Mail Website
Guest Editor
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, China
Interests: cycloaddition; nitrones; N-O bond cleavage; medium-sized ring formation; rearrangement
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Ye Wei

E-Mail Website
Guest Editor
Chongqing Key Laboratory of Soft-Matter Material Chemistry and Function Manufacturing, Southwest University, Chongqing 400715, China
Interests: radical relay annulation; heterocycle synthesis, N-O bond transformations, organo/metal synergistic catalysis

Special Issue Information

Dear Colleagues,

N−O bond compounds, such as O-aryloxime ethers, O-alkenyloxime ethers, nitrones and N-oxides, etc., are not only important functional groups in various natural products, pharmaceuticals, agriculture, and molecular drug design, but also key precursors to access various heterocycles. Those N-O bond transformations involving cycloaddition, cyclization, reduction, oxidation, rearrangement, and radical cascade reactions are highly desired.

In this Special Issue, we welcome contributions on the application of N-O bond compounds from various fields, including the formation of N-O bonds, N-O bond functionalization, N-O bond cleavage, and properties of N-O bond molecules. The reactions can occur at any element or any functional groups involving metal-free conditions, metal catalysis, organocatalysis, heterocatalysis or homocatalysis, photocatalysis or electrocatalysis, or their applications in the construction of important heterocycles.

Within the scope of the application of N-O bond compounds, potential topics about N-O bonds include the design and synthesis of catalysts, the development of new catalytic systems, organic synthetic methodologies, mechanistic studies, and the synthesis of natural products or pharmaceutical intermediates. We welcome full papers, communications, and comprehensive reviews.

Prof. Dr. Dongliang Mo
Prof. Dr. Ye Wei
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

  • cycloaddition
  • cyclization
  • N-O bond cleavage
  • N-functionalization
  • O-functionalization
  • difunctionalization
  • N-O reduction
  • N-O oxidation
  • aza-heterocycle

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Published Papers (6 papers)

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Research

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11 pages, 2368 KiB  
Article
Synthesis of meta-Aminophenol Derivatives via Cu-Catalyzed [1,3]-Rearrangement—Oxa-Michael Addition Cascade Reactions
by Itaru Nakamura, Mai Tachibana, Riku Konta, Hiroki Tashiro and Masahiro Terada
Molecules 2023, 28(10), 4251; https://doi.org/10.3390/molecules28104251 - 22 May 2023
Cited by 1 | Viewed by 2090
Abstract
Cu-catalyzed reactions of N-alkoxy-2-methylanilines and alcohols in the presence of catalytic amounts of IPrCuBr and AgSbF6 afforded the corresponding meta-aminophenol derivatives in good to high yields. These reactions proceed via a [1,3]-rearrangement, in which the alkoxy group migrates from the [...] Read more.
Cu-catalyzed reactions of N-alkoxy-2-methylanilines and alcohols in the presence of catalytic amounts of IPrCuBr and AgSbF6 afforded the corresponding meta-aminophenol derivatives in good to high yields. These reactions proceed via a [1,3]-rearrangement, in which the alkoxy group migrates from the nitrogen atom to the methyl-substituted ortho position, followed by an oxa-Michael reaction of the resulting ortho-quinol imine intermediate. Full article
(This article belongs to the Special Issue Advances on the Application of N-O Bond Compounds)
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13 pages, 1161 KiB  
Article
Urea Synthesis from Isocyanides and O-Benzoyl Hydroxylamines Catalyzed by a Copper Salt
by Ning Yu, Jing-Fang Lv, Shi-Mei He, Yanyan Cui, Ye Wei and Kun Jiang
Molecules 2022, 27(23), 8219; https://doi.org/10.3390/molecules27238219 - 25 Nov 2022
Cited by 1 | Viewed by 1668
Abstract
In the presence of CuOAc, a series of unsymmetric ureas can be generated in moderate to good yields under mild reaction conditions (10 mol% of CuOAc, 2 equiv t-BuONa or PhONa, 30 °C), using aryl isocyanides and O-benzoyl hydroxylamines as the [...] Read more.
In the presence of CuOAc, a series of unsymmetric ureas can be generated in moderate to good yields under mild reaction conditions (10 mol% of CuOAc, 2 equiv t-BuONa or PhONa, 30 °C), using aryl isocyanides and O-benzoyl hydroxylamines as the readily accessible starting materials. The reactions might undergo a cascade process involving isocyanide insertion into the N-O bond and Mumm-type rearrangement. This work represents a rare example of isocyanide insertion into N-O bonds, which would extend isocyanide insertion chemistry. Full article
(This article belongs to the Special Issue Advances on the Application of N-O Bond Compounds)
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Review

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22 pages, 5009 KiB  
Review
Recent Advances in the Synthesis of Di- and Trisubstituted Hydroxylamines
by Jarvis Hill, Thomas D. Beckler and David Crich
Molecules 2023, 28(6), 2816; https://doi.org/10.3390/molecules28062816 - 21 Mar 2023
Cited by 9 | Viewed by 4517
Abstract
As an underrepresented functional group in bioorganic and medicinal chemistry, the hydroxylamine unit has historically received little attention from the synthetic community. Recent developments, however, suggest that hydroxylamines may have broader applications such that a review covering recent developments in the synthesis of [...] Read more.
As an underrepresented functional group in bioorganic and medicinal chemistry, the hydroxylamine unit has historically received little attention from the synthetic community. Recent developments, however, suggest that hydroxylamines may have broader applications such that a review covering recent developments in the synthesis of this functional group is timely. With this in mind, this review primarily covers developments in the past 15 years in the preparation of di- and trisubstituted hydroxylamines. The mechanism of the reactions and key features and shortcomings are discussed throughout the review. Full article
(This article belongs to the Special Issue Advances on the Application of N-O Bond Compounds)
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33 pages, 6474 KiB  
Review
Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters
by Pu Chen, Huawen Huang, Qi Tan, Xiaochen Ji and Feng Zhao
Molecules 2023, 28(6), 2667; https://doi.org/10.3390/molecules28062667 - 15 Mar 2023
Cited by 6 | Viewed by 3732
Abstract
The synthetic strategies of oxime derivatives participating in radical-type reactions have been rapidly developed in the last few decades. Among them, the N–O bond cleavage of oxime esters leading to formation of nitrogen-centered radicals triggers adjacent C–C bond cleavage to produce carbon-centered free [...] Read more.
The synthetic strategies of oxime derivatives participating in radical-type reactions have been rapidly developed in the last few decades. Among them, the N–O bond cleavage of oxime esters leading to formation of nitrogen-centered radicals triggers adjacent C–C bond cleavage to produce carbon-centered free radicals, which has been virtually used in organic synthesis in recent years. Herein, we summarized the radical reactions involving oxime N–O bond and C–C bond cleavage through this special reaction form, including those from acyl oxime ester derivatives and cyclic ketoxime ester derivatives. These contents were systematically classified according to different reaction types. In this review, the free radical reactions involving acyl oxime esters and cyclic ketoxime esters after 2021 were included, with emphasis on the substrate scope and reaction mechanism. Full article
(This article belongs to the Special Issue Advances on the Application of N-O Bond Compounds)
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Scheme 1

23 pages, 9038 KiB  
Review
Recent Advances in N-O Bond Cleavage of Oximes and Hydroxylamines to Construct N-Heterocycle
by Hui-Min Jiang, Yi-Lin Zhao, Qing Sun, Xuan-Hui Ouyang and Jin-Heng Li
Molecules 2023, 28(4), 1775; https://doi.org/10.3390/molecules28041775 - 13 Feb 2023
Cited by 13 | Viewed by 4375
Abstract
Oximes and hydroxylamines are a very important class of skeletons that not only widely exist in natural products and drug molecules, but also a class of synthon, which have been widely used in industrial production. Due to weak N-O σ bonds of oximes [...] Read more.
Oximes and hydroxylamines are a very important class of skeletons that not only widely exist in natural products and drug molecules, but also a class of synthon, which have been widely used in industrial production. Due to weak N-O σ bonds of oximes and hydroxylamines, they can be easily transformed into other functional groups by N-O bond cleavage. Therefore, the synthesis of N-heterocycle by using oximes and hydroxylamines as nitrogen sources has attracted wide attention. Recent advances for the synthesis of N-heterocycle through transition-metal-catalyzed and radical-mediated cyclization classified by the type of nitrogen sources and rings are summarized. In this paper, the recent advances in the N-O bond cleavage of oximes and hydroxylamines are reviewed. We hope that this review provides a new perspective on this field, and also provides a reference to develop environmentally friendly and sustainable methods. Full article
(This article belongs to the Special Issue Advances on the Application of N-O Bond Compounds)
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20 pages, 4767 KiB  
Review
Interrupted Nef and Meyer Reactions: A Growing Point for Diversity-Oriented Synthesis Based on Nitro Compounds
by Alexey Yu. Sukhorukov
Molecules 2023, 28(2), 686; https://doi.org/10.3390/molecules28020686 - 10 Jan 2023
Cited by 14 | Viewed by 3679
Abstract
The Nef reaction (nitro to carbonyl group conversion) and related Meyer reaction are among the key transformations of aliphatic nitro compounds. The interrupted versions of these reactions in which the normal pathway is redirected to a different end product by an external nucleophile [...] Read more.
The Nef reaction (nitro to carbonyl group conversion) and related Meyer reaction are among the key transformations of aliphatic nitro compounds. The interrupted versions of these reactions in which the normal pathway is redirected to a different end product by an external nucleophile are much less common, albeit these processes substantially increase the synthetic potential of nitro compounds. In this review, examples of interrupted Nef and Meyer reactions are summarized, and the prospects of this methodology in diversity-oriented organic synthesis are analyzed. The bibliography contains 90 references. Full article
(This article belongs to the Special Issue Advances on the Application of N-O Bond Compounds)
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