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Nitro Compounds and Their Derivatives in Organic Synthesis
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Nitro Compounds and Their Derivatives in Organic Synthesis

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

Deadline for manuscript submissions: closed (30 April 2020) | Viewed by 34126

Printed Edition Available!
A printed edition of this Special Issue is available here.

Special Issue Editor

Prof. Dr. Nagatoshi Nishiwaki

E-Mail Website1 Website2
Guest Editor
School of Environmental Science and Engineering, Kochi University of Technology Tosayamada, Kami, Kochi, Japan
Interests: organic synthesis; heterocyclic chemistry; synthesis of polyfunctionalized compounds; cycloaddition; nitro chemistry; pseudo-intramolecular proces

Special Issue Information

Dear Colleagues,

Nitro compounds constitute a large family among organic compounds and are widely used for various purposes. The versatility of these compounds is largely due to the diverse properties of their nitro functionality. Nitro groups considerably decrease electron density of the scaffold framework by both inductive and resonance electron-withdrawing effects to facilitate reactions with nucleophiles or transfer of single electron. The α-hydrogen of a nitro group is highly acidic, leading to a stable nitronate anion, which facilitates reactions of nitroalkanes with both electrophilic and nucleophilic reagents. Nitro groups also assist the cleavage of an adjacent carbon–carbon bond. Furthermore, nitro groups can be transformed into versatile functional groups. Despite the substantial contributions of many researchers to nitro chemistry, the chemistry of nitro groups is still an exciting and challenging research area. Thanks to the open access platform, this Special Issue will be an open forum where researchers may share their investigations and findings in this promising field. Contributions to this issue, both in the form of original research or review articles, may cover all aspects of organic synthesis using a nitro group; papers addressing the development of functional materials such as medicines and fluorescence compounds, are particularly welcome.

Prof. Nagatoshi Nishiwaki
Guest Editor

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Keywords

  • Nitro compounds
  • Organic synthesis
  • Michael acceptor
  • Cycloaddition
  • Cross-coupling
  • Chemical transformation
  • Safety and handleability
  • Functional materials
  • Pharmacy
  • Fluorescence and quenching

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Published Papers (8 papers)

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Editorial

Jump to: Research, Review

5 pages, 190 KiB  
Editorial
A Walk through Recent Nitro Chemistry Advances
by Nagatoshi Nishiwaki
Molecules 2020, 25(16), 3680; https://doi.org/10.3390/molecules25163680 - 12 Aug 2020
Cited by 28 | Viewed by 4354
Abstract
Chemistry of nitro groups and nitro compounds has long been intensively studied. Despite their long history, new reactions and methodologies are still being found today. This is due to the diverse reactivity of the nitro group. The importance of nitro chemistry will continue [...] Read more.
Chemistry of nitro groups and nitro compounds has long been intensively studied. Despite their long history, new reactions and methodologies are still being found today. This is due to the diverse reactivity of the nitro group. The importance of nitro chemistry will continue to increase in the future in terms of elaborate synthesis. In this article, we will take a walk through the recent advances in nitro chemistry that have been made in past decades. Full article
(This article belongs to the Special Issue Nitro Compounds and Their Derivatives in Organic Synthesis)

Research

Jump to: Editorial, Review

13 pages, 1804 KiB  
Article
The Cyclic Nitronate Route to Pharmaceutical Molecules: Synthesis of GSK’s Potent PDE4 Inhibitor as a Case Study
by Evgeny V. Pospelov, Ivan S. Golovanov, Sema L. Ioffe and Alexey Yu. Sukhorukov
Molecules 2020, 25(16), 3613; https://doi.org/10.3390/molecules25163613 - 8 Aug 2020
Cited by 8 | Viewed by 3645
Abstract
An efficient asymmetric synthesis of GlaxoSmithKline’s potent PDE4 inhibitor was accomplished in eight steps from a catechol-derived nitroalkene. The key intermediate (3-acyloxymethyl-substituted 1,2-oxazine) was prepared in a straightforward manner by tandem acylation/(3,3)-sigmatropic rearrangement of the corresponding 1,2-oxazine-N-oxide. The latter was assembled [...] Read more.
An efficient asymmetric synthesis of GlaxoSmithKline’s potent PDE4 inhibitor was accomplished in eight steps from a catechol-derived nitroalkene. The key intermediate (3-acyloxymethyl-substituted 1,2-oxazine) was prepared in a straightforward manner by tandem acylation/(3,3)-sigmatropic rearrangement of the corresponding 1,2-oxazine-N-oxide. The latter was assembled by a (4 + 2)-cycloaddition between the suitably substituted nitroalkene and vinyl ether. Facile acetal epimerization at the C-6 position in 1,2-oxazine ring was observed in the course of reduction with NaBH3CN in AcOH. Density functional theory (DFT) calculations suggest that the epimerization may proceed through an unusual tricyclic oxazolo(1,2)oxazinium cation formed via double anchimeric assistance from a distant acyloxy group and the nitrogen atom of the 1,2-oxazine ring. Full article
(This article belongs to the Special Issue Nitro Compounds and Their Derivatives in Organic Synthesis)
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9 pages, 1765 KiB  
Communication
Synthesis and Properties of NitroHPHAC: The First Example of Substitution Reaction on HPHAC
by Yoshiki Sasaki, Masayoshi Takase, Shigeki Mori and Hidemitsu Uno
Molecules 2020, 25(11), 2486; https://doi.org/10.3390/molecules25112486 - 27 May 2020
Cited by 8 | Viewed by 3252
Abstract
Hexapyrrolohexaazacoronene (HPHAC) is one of the N-containing polycyclic aromatic hydrocarbons in which six pyrroles are fused circularly around a benzene. Despite the recent development of HPHAC analogues, there is no report on direct introduction of functional groups into the HPHAC skeleton. This work [...] Read more.
Hexapyrrolohexaazacoronene (HPHAC) is one of the N-containing polycyclic aromatic hydrocarbons in which six pyrroles are fused circularly around a benzene. Despite the recent development of HPHAC analogues, there is no report on direct introduction of functional groups into the HPHAC skeleton. This work reports the first example of nitration reaction of decaethylHPHAC. The structures of nitrodecaethylHPHAC including neutral and two oxidized species (radical cation and dication), intramolecular charge transfer (ICT) character, and global aromaticity of the dication are discussed. Full article
(This article belongs to the Special Issue Nitro Compounds and Their Derivatives in Organic Synthesis)
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Graphical abstract

15 pages, 3456 KiB  
Article
Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-b]pyridines
by Maxim A. Bastrakov, Alexey K. Fedorenko, Alexey M. Starosotnikov, Ivan V. Fedyanin and Vladimir A. Kokorekin
Molecules 2020, 25(9), 2194; https://doi.org/10.3390/molecules25092194 - 8 May 2020
Cited by 9 | Viewed by 2818
Abstract
A number of novel 6-R-isoxazolo[4,3-b]pyridines were synthesized and their reactions with neutral C-nucleophiles (1,3-dicarbonyl compounds, π-excessive (het)arenes, dienes) were studied. The reaction rate was found to be dependent on the nature of the substituent 6-R. The most reactive 6-nitroisoxazolo[4,3-b]pyridines [...] Read more.
A number of novel 6-R-isoxazolo[4,3-b]pyridines were synthesized and their reactions with neutral C-nucleophiles (1,3-dicarbonyl compounds, π-excessive (het)arenes, dienes) were studied. The reaction rate was found to be dependent on the nature of the substituent 6-R. The most reactive 6-nitroisoxazolo[4,3-b]pyridines are able to add C-nucleophiles in the absence of a base under mild conditions. In addition, these compounds readily undergo [4+2]-cycloaddition reactions on aromatic bonds C=C(NO2) of the pyridine ring, thus indicating the superelectrophilic nature of 6-NO2-isoxazolo[4,3-b]pyridines. Full article
(This article belongs to the Special Issue Nitro Compounds and Their Derivatives in Organic Synthesis)
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Graphical abstract

9 pages, 1023 KiB  
Article
Comparison of Substituting Ability of Nitronate versus Enolate for Direct Substitution of a Nitro Group
by Yusuke Mukaijo, Soichi Yokoyama and Nagatoshi Nishiwaki
Molecules 2020, 25(9), 2048; https://doi.org/10.3390/molecules25092048 - 28 Apr 2020
Cited by 9 | Viewed by 3617
Abstract
α-Nitrocinnamate underwent the conjugate addition of an active methylene compound such as nitroacetate, 1,3-dicarbonyl compound, or α-nitroketone, and the following ring closure afforded functionalized heterocyclic frameworks. The reaction of cinnamate with nitroacetate occurs via nucleophilic substitution of a nitro group by the O [...] Read more.
α-Nitrocinnamate underwent the conjugate addition of an active methylene compound such as nitroacetate, 1,3-dicarbonyl compound, or α-nitroketone, and the following ring closure afforded functionalized heterocyclic frameworks. The reaction of cinnamate with nitroacetate occurs via nucleophilic substitution of a nitro group by the O-attack of the nitronate, which results in isoxazoline N-oxide. This protocol was applicable to 1,3-dicarbonyl compounds to afford dihydrofuran derivatives, including those derived from direct substitution of a nitro group caused by O-attack of enolate. It was found the reactivity was lowered by an electron-withdrawing group on the carbonyl moiety. When α-nitroketone was employed as a substrate, three kinds of products were possibly formed; of these, only isoxazoline N-oxide was identified. This result indicates that the substituting ability of nitronate is higher than that of enolate for the direct SN2 substitution of a nitro group. Full article
(This article belongs to the Special Issue Nitro Compounds and Their Derivatives in Organic Synthesis)
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10 pages, 2166 KiB  
Article
Phenacylation of 6-Methyl-Beta-Nitropyridin-2-Ones and Further Heterocyclization of Products
by Eugene V. Babaev and Victor B. Rybakov
Molecules 2020, 25(7), 1682; https://doi.org/10.3390/molecules25071682 - 7 Apr 2020
Cited by 2 | Viewed by 2691
Abstract
Reaction between the derivatives of 6-methyl-beta-nitropyridin-2-one and phenacyl bromides was studied, and the yields observed were extremely low. The pyridones were converted via chloropyridines to methoxyderivatives, which were N-phenacylated. N-Phenacyl derivatives of 4,6-dimethyl-5-nitropyridin-2-one under the action of base gave 5-hydroxy-8-nitroindolizine and under [...] Read more.
Reaction between the derivatives of 6-methyl-beta-nitropyridin-2-one and phenacyl bromides was studied, and the yields observed were extremely low. The pyridones were converted via chloropyridines to methoxyderivatives, which were N-phenacylated. N-Phenacyl derivatives of 4,6-dimethyl-5-nitropyridin-2-one under the action of base gave 5-hydroxy-8-nitroindolizine and under acidic conditions gave 5-methyl-6-nitrooxazole[3,2-a]pyridinium salt, which underwent recycization with MeONa to 5-methoxy-8-nitroindolizine. Full article
(This article belongs to the Special Issue Nitro Compounds and Their Derivatives in Organic Synthesis)
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Review

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17 pages, 3481 KiB  
Review
Nitro-Perylenediimide: An Emerging Building Block for the Synthesis of Functional Organic Materials
by Lou Rocard, Antoine Goujon and Piétrick Hudhomme
Molecules 2020, 25(6), 1402; https://doi.org/10.3390/molecules25061402 - 19 Mar 2020
Cited by 32 | Viewed by 7107
Abstract
Perylenediimide (PDI) is one of the most important classes of dyes and is intensively explored in the field of functional organic materials. The functionalization of this electron-deficient aromatic core is well-known to tune the outstanding optoelectronic properties of PDI derivatives. In this respect, [...] Read more.
Perylenediimide (PDI) is one of the most important classes of dyes and is intensively explored in the field of functional organic materials. The functionalization of this electron-deficient aromatic core is well-known to tune the outstanding optoelectronic properties of PDI derivatives. In this respect, the functionalization has been mostly addressed in bay-positions to halogenated derivatives through nucleophilic substitutions or metal-catalyzed coupling reactions. Being aware of the synthetic difficulties of obtaining the key intermediate 1-bromoPDI, we will present as an alternative in this review the potential of 1-nitroPDI: a powerful building block to access a large variety of PDI-based materials. Full article
(This article belongs to the Special Issue Nitro Compounds and Their Derivatives in Organic Synthesis)
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25 pages, 7329 KiB  
Review
Recent Progress in Nitro-Promoted Direct Functionalization of Pyridones and Quinolones
by Feiyue Hao and Nagatoshi Nishiwaki
Molecules 2020, 25(3), 673; https://doi.org/10.3390/molecules25030673 - 5 Feb 2020
Cited by 11 | Viewed by 3943
Abstract
Nitro group is one of the most important functional groups in organic syntheses because its strongly electron-withdrawing ability activates the scaffold, facilitating the reaction with nucleophilic reagents or the Diels–Alder reaction. In this review, recent progress in the nitro-promoted direct functionalization of pyridones [...] Read more.
Nitro group is one of the most important functional groups in organic syntheses because its strongly electron-withdrawing ability activates the scaffold, facilitating the reaction with nucleophilic reagents or the Diels–Alder reaction. In this review, recent progress in the nitro-promoted direct functionalization of pyridones and quinolones is highlighted to complement previous reviews. Full article
(This article belongs to the Special Issue Nitro Compounds and Their Derivatives in Organic Synthesis)
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