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Amide Bond Activation II

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

Deadline for manuscript submissions: closed (15 September 2021) | Viewed by 6659

Special Issue Editor


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Guest Editor
Department of Chemistry, Rutgers University, 73 Warren St., Newark, NJ 07102, USA
Interests: amide bonds; N-heterocyclic carbenes; C-N activation; C-H activation; C-O activation; lanthanides; cross-coupling; catalysis; reductions; reductive couplings; radical chemistry; synthetic methodology; natural products
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

In 2018, we edited the Special Issue "Amide Bond Activation" of Molecules. After peer review, 24 excellent papers were published addressing various aspects of amide bonds and amide bond activation. Amide bonds are of interest to the broad audience of the journal. Therefore, we decided to establish a Special Issue Series on this topic and launch the second Special Issue, namely "Amide Bond Activation II"

The amide bond represents a privileged motif in chemistry. One fascinating feature of the amide bond is the innate stability achieved by delocalization of the nitrogen lone pair into the carbonyl group. Defying conventional knowledge that characterizes the amide bond as one of the most robust functional groups in synthetic chemistry, recent years have witnessed an explosion of interest in the development of new chemical transformations of amides. An important trend involves chemoselective activation of the N–C amide bond by metal insertion. This thriving class of reactions originates from the classic studies on amide bond destabilization and has the potential to become a widely applicable cross-coupling platform. More generally, N–C bond activation emphasizes the significance of ubiquitous amide bonds to participate in a wide range of electrophilic, Lewis acid, radical, and nucleophilic reaction pathways, among other transformations. These methods are beneficial to chemists because they supply valuable compounds by functional group interconversion or functionalization of amides on the fundamental level. Equally relevant are structural and theoretical studies that provide the basis for chemoselective manipulation of amidic resonance. This Special Issue will provide a broad survey of recent advances in the activation of amides and address various approaches in the field. This Special Issue will contain contributions describing multifaceted aspects of this field. Review articles by experts in the field are also welcome.

Prof. Dr. Michal Szostak
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

  • Amides
  • Amide bond
  • Bond functionalization
  • Functional group interconversion
  • Organic synthesis
  • Cross-coupling
  • Catalysis
  • N–C activation
  • Esters
  • O–C activation
  • Resonance
  • Planarity
  • Winkler-Dunitz parameters
  • Twisted amides

Published Papers (2 papers)

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Research

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14 pages, 6040 KiB  
Article
Design, Synthesis, and Bioactivity Evaluation of New Thiochromanone Derivatives Containing a Carboxamide Moiety
by Lingling Xiao, Lu Yu, Pei Li, Jiyan Chi, Zhangfei Tang, Jie Li, Shuming Tan and Xiaodan Wang
Molecules 2021, 26(15), 4391; https://doi.org/10.3390/molecules26154391 - 21 Jul 2021
Cited by 6 | Viewed by 2018
Abstract
In this study, using the botanical active component thiochromanone as the lead compound, a total of 32 new thiochromanone derivatives containing a carboxamide moiety were designed and synthesized and their in vitro antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas [...] Read more.
In this study, using the botanical active component thiochromanone as the lead compound, a total of 32 new thiochromanone derivatives containing a carboxamide moiety were designed and synthesized and their in vitro antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas oryzae pv. oryzicolaby (Xoc), and Xanthomonas axonopodis pv. citri (Xac) were determined, as well as their in vitro antifungal activities against Botryosphaeria dothidea (B. dothidea), Phomopsis sp., and Botrytis cinerea (B. cinerea). Bioassay results demonstrated that some of the target compounds exhibited moderate to good in vitro antibacterial and antifungal activities. In particular, compound 4e revealed excellent in vitro antibacterial activity against Xoo, Xoc, and Xac, and its EC50 values of 15, 19, and 23 μg/mL, respectively, were superior to those of Bismerthiazol and Thiodiazole copper. Meanwhile, compound 3b revealed moderate in vitro antifungal activity against B. dothidea at 50 μg/mL, and the inhibition rate reached 88%, which was even better than that of Pyrimethanil, however, lower than that of Carbendazim. To the best of our knowledge, this is the first report on the antibacterial and antifungal activities of this series of novel thiochromanone derivatives containing a carboxamide moiety. Full article
(This article belongs to the Special Issue Amide Bond Activation II)
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Review

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50 pages, 14810 KiB  
Review
A Journey from June 2018 to October 2021 with N,N-Dimethylformamide and N,N-Dimethylacetamide as Reactants
by Jacques Muzart
Molecules 2021, 26(21), 6374; https://doi.org/10.3390/molecules26216374 - 21 Oct 2021
Cited by 6 | Viewed by 3721
Abstract
A rich array of reactions occur using N,N-dimethylformamide (DMF) or N,N-dimethylacetamide (DMAc) as reactants, these two amides being able to deliver their own H, C, N, and O atoms for the synthesis of a variety of compounds. [...] Read more.
A rich array of reactions occur using N,N-dimethylformamide (DMF) or N,N-dimethylacetamide (DMAc) as reactants, these two amides being able to deliver their own H, C, N, and O atoms for the synthesis of a variety of compounds. This account highlights the literature published since June 2018, completing previous reviews by the author. Full article
(This article belongs to the Special Issue Amide Bond Activation II)
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