scholarly journals Greener Synthesis of Nitrogen-Containing Heterocycles in Water, PEG, and Bio-Based Solvents

Catalysts ◽  
2020 ◽  
Vol 10 (4) ◽  
pp. 429
Author(s):  
Joana F. Campos ◽  
Sabine Berteina-Raboin
Keyword(s):  
Organic Chemistry ◽  
Environmental Performance ◽  
Ecological Impact ◽  
Nitrogen Heterocycles ◽  
Chemical Transformations ◽  
Pharmaceutical Drugs ◽  
Wide Scope ◽  
Green Solvents ◽  
Health Safety ◽  
Greener Synthesis

The solvents used in chemistry are a fundamental element of the environmental performance of processes in corporate and academic laboratories. Their influence on costs, health safety, and nature cannot be neglected. Quantitatively, solvents are the most abundant constituents of chemical transformations; therefore, acting on solvents and replacing standard solvents with safer products can have a great ecological impact. However, not all green solvents are suitable for the wide scope of organic chemistry reactions. A second point to consider is that 50% of pharmaceutical drugs are nitrogen heterocycles compounds. It therefore appeared important to provide an overview of the more ecological methodologies for synthesizing this class of compounds. In this review, all publications since 2000 that describe green reactions leading to the formation of nitrogen heterocycles using safe solvents were considered. We chose water, PEG, and bio-based solvents for their negligible toxicity. The synthesis of five-, six-, and seven-membered aromatic nitrogen heterocycles using green reactions reported in the literature to date is described.

scholarly journals Eucalyptol, an All-Purpose Product

Catalysts ◽  
2022 ◽  
Vol 12 (1) ◽  
pp. 48
Author(s):  
Joana F. Campos ◽  
Sabine Berteina-Raboin
Keyword(s):  
Organic Chemistry ◽  
Environmental Impact ◽  
Environmental Performance ◽  
Good Alternative ◽  
Optimization Process ◽  
Coupling Reactions ◽  
Green Solvents ◽  
Safety And Health ◽  
The Ideal

Eucalyptus plants have attracted the attention of researchers and environmentalists worldwide because they are a rapidly growing source of wood and a source of oil used for multiple purposes. The main and the most important oil component is 1,8-cineole (eucalyptol: 60%–85%). This review summarizes the literature reported to date involving the use of 1,8-cineole for the treatment of disorders. Additionally, we describe our efforts in the use of eucalyptol as a solvent for the synthesis of O,S,N-heterocycles. Solvents used in chemistry are a fundamental element of the environmental performance of processes in corporate and academic laboratories. Their influence on costs, safety and health cannot be neglected. Green solvents such as bio-based systems hold considerable additional promise to reduce the environmental impact of organic chemistry. The first section outlines the process leading to our discovery of an unprecedented solvent and its validation in the first coupling reactions. This section continues with the description of its properties and characteristics and its reuse as reported in the various studies conducted. The second section highlights the use of eucalyptol in a series of coupling reactions (i.e., Suzuki–Miyaura, Sonogashira–Hagihara, Buchwald–Hartwig, Migita–Kosugi–Stille, Hiyama and cyanation) that form O,S,N-heterocycles. We describe the optimization process applied to reach the ideal conditions. We also show that eucalyptol can be a good alternative to build heterocycles that contain oxygen, sulfur and nitrogen. These studies allowed us to demonstrate the viability and potential that bio solvents can have in synthesis laboratories.

Transition metal-catalyzed sp3 C–H activation and intramolecular C–N coupling to construct nitrogen heterocyclic scaffolds

2019 ◽  
Vol 55 (87) ◽  
pp. 13048-13065 ◽  
Author(s):  
Ming Zhang ◽  
Qiuhong Wang ◽  
Yiyuan Peng ◽  
Zhiyuan Chen ◽  
Changfeng Wan ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Transition Metal ◽  
Nitrogen Heterocycles ◽  
Synthetic Organic Chemistry ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Nitrogen Heterocyclic

Nitrogen heterocycles are of great medicinal importance, and the construction of nitrogen heterocyclic scaffolds has been one of the focuses in synthetic organic chemistry.

scholarly journals Heterogeneous acidic catalysts for the tetrahydropyranylation of alcohols and phenols in green ethereal solvents

2018 ◽  
Vol 14 ◽  
pp. 1655-1659 ◽  
Author(s):  
Ugo Azzena ◽  
Massimo Carraro ◽  
Gloria Modugno ◽  
Luisa Pisano ◽  
Luigi Urtis
Keyword(s):  
Organic Chemistry ◽  
Heterogeneous Catalysis ◽  
Important Class ◽  
Green Solvents ◽  
Reaction Products ◽  
Reaction Conditions ◽  
One Pot ◽  
Acidic Catalysts ◽  
Set Up ◽  
Work Up

The application of heterogeneous catalysis and green solvents to the set up of widely employed reactions is a challenge in contemporary organic chemistry. We applied such an approach to the synthesis and further conversion of tetrahydropyranyl ethers, an important class of compounds widely employed in multistep syntheses. Several alcohols and phenols were almost quantitatively converted into the corresponding tetrahydropyranyl ethers in cyclopentyl methyl ether or 2-methyltetrahydrofuran employing NH4HSO4 supported on SiO2 as a recyclable acidic catalyst. Easy work up of the reaction mixtures and the versatility of the solvents allowed further conversion of the reaction products under one-pot reaction conditions.

scholarly journals A Study of Catalytic Oxidation of a Library of C2 to C4 Alcohols in the Presence of Nanogold

Nanomaterials ◽  
2019 ◽  
Vol 9 (3) ◽  
pp. 442
Author(s):  
Maciej Kapkowski ◽  
Anna Niemczyk-Wojdyla ◽  
Piotr Bartczak ◽  
Monika Pyrkosz Bulska ◽  
Kamila Gajcy ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Green Chemistry ◽  
Alcohol Oxidation ◽  
Catalytic Performance ◽  
Toxic Chemicals ◽  
Wide Scope ◽  
Catalytic Potential ◽  
Green Oxidation ◽  
Oxidation Of Alcohols ◽  
Different Levels

The classical stoichiometric oxidation of alcohols is an important tool in contemporary organic chemistry. However, it still requires huge modifications in order to comply with the principles of green chemistry. The use of toxic chemicals, hazardous organic solvents, and the large amounts of toxic wastes that result from the reactions are a few examples of the problems that must be solved. Nanogold alone or conjugated with palladium were supported on different carriers (SiO2, C) and investigated in order to evaluate their catalytic potential for environmentally friendly alcohol oxidation under solvent-free and base-free conditions in the presence H2O2 as a clean oxidant. We tested different levels of Au loading (0.1–1.2% wt.) and different active catalytic site forms (monometallic Au or bimetallic Au–Pd sites). This provided new insights on how the structure of the Au-dispersions affected their catalytic performance. Importantly, the examination of the catalytic performance of the resulting catalysts was oriented toward a broad scope of alcohols, including those that are the most resistant to oxidation—the primary aliphatic alcohols. Surprisingly, the studies proved that Au/SiO2 at a level of Au loading as low as 0.1% wt. appeared to be efficient and prospective catalytic system for the green oxidation of alcohol. Most importantly, the results revealed that 0.1% Au/SiO2 might be the catalyst of choice with a wide scope of utility in the green oxidation of various structurally different alcohols as well as the non-activated aliphatic ones.

scholarly journals Fused 1,5-Naphthyridines: Synthetic Tools and Applications

Molecules ◽  
2020 ◽  
Vol 25 (15) ◽  
pp. 3508
Author(s):  
Carme Masdeu ◽  
Maria Fuertes ◽  
Endika Martin-Encinas ◽  
Asier Selas ◽  
Gloria Rubiales ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Biological Activity ◽  
Metal Complexes ◽  
Biological Activities ◽  
Nitrogen Heterocycles ◽  
Diels Alder ◽  
Nitrogen Compounds ◽  
Wide Range ◽  
Oxygen Heterocycles ◽  
Optical Applications

Heterocyclic nitrogen compounds, including fused 1,5-naphthyridines, have versatile applications in the fields of synthetic organic chemistry and play an important role in the field of medicinal chemistry, as many of them have a wide range of biological activities. In this review, a wide range of synthetic protocols for the construction of this scaffold are presented. For example, Friedländer, Skraup, Semmlere-Wolff, and hetero-Diels-Alder, among others, are well known classical synthetic protocols used for the construction of the main 1,5-naphthyridine scaffold. These syntheses are classified according to the nature of the cycle fused to the 1,5-naphthyridine ring: carbocycles, nitrogen heterocycles, oxygen heterocycles, and sulphur heterocycles. In addition, taking into account the aforementioned versatility of these heterocycles, their reactivity is presented as well as their use as a ligand for metal complexes formation. Finally, those fused 1,5-naphthyridines that present biological activity and optical applications, among others, are indicated.

scholarly journals Recent applications of imines as key intermediates in the synthesis of alkaloids and novel nitrogen heterocycles

2009 ◽  
Vol 81 (2) ◽  
pp. 195-204 ◽  
Author(s):  
Stephen F. Martin
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Multicomponent Reactions ◽  
Nitrogen Heterocycles ◽  
Biologically Active ◽  
Total Syntheses ◽  
Biological Interest ◽  
Cascade Processes ◽  
Novel Applications ◽  
Active Natural

One of the major challenges in contemporary synthetic organic chemistry is the design and development of new tactics and strategies and their application to concise and efficient syntheses of biologically active natural products. Strategies that utilize reactions that enable the rapid assembly of the skeletal framework of such targets are thus especially attractive. In this context, we have developed novel applications of imine chemistry in Mannich and related reactions, cascade processes, and multicomponent reactions (MCRs) to rapidly assemble structural subunits common to diverse families of alkaloids. The practical utility of these chemistries is evidenced by their use in the execution of facile total syntheses of (±)-epilupinine (1), (±)-tashiromine (2), (-)-epimyrtine (3), and (±)-roelactamine (4) as well as other nitrogen heterocycles of potential biological interest.

scholarly journals 15N labeling and analysis of 13C–15N and 1H–15N couplings in studies of the structures and chemical transformations of nitrogen heterocycles

RSC Advances ◽  
2019 ◽  
Vol 9 (46) ◽  
pp. 26856-26879 ◽  
Author(s):  
Sergey L. Deev ◽  
Igor A. Khalymbadzha ◽  
Tatyana S. Shestakova ◽  
Valery N. Charushin ◽  
Oleg N. Chupakhin
Keyword(s):  
Nitrogen Heterocycles ◽  
Chemical Transformations ◽  
15N Labeling ◽  
Structural Aspects

This review provides a generalization of effective examples of 15N labeling followed by an analysis of JCN and JHN couplings in solution as a tool to study the structural aspects and pathways of chemical transformations in nitrogen heterocycles.

Ethenesulfonyl Fluoride (ESF) and Its Derivatives in SuFEx Click Chemistry and More

Synthesis ◽  
2019 ◽  
Vol 52 (05) ◽  
pp. 673-687 ◽  
Author(s):  
Yan-Ping Meng ◽  
Shi-Meng Wang ◽  
Wan-Yin Fang ◽  
Zhi-Zhong Xie ◽  
Jing Leng ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Click Chemistry ◽  
Exchange Reaction ◽  
Organic Synthesis ◽  
Medicinal Chemistry ◽  
Materials Science ◽  
Click Reaction ◽  
Chemical Properties ◽  
Chemical Transformations ◽  
Absolute Reliability

The sulfur(VI) fluoride exchange reaction (SuFEx), developed by Sharpless and co-workers in 2014, is a new category of click reaction that creates molecular connections with absolute reliability and unprecedented efficiency through a sulfur(VI) hub. Ethenesulfonyl fluoride (ESF), as one of the most important sulfur(VI) hubs, exhibits extraordinary reactivity in SuFEx click chemistry and organic synthesis. This review summarizes the chemical properties and applications of ESF in click chemistry, organic chemistry, materials science, medicinal chemistry and in many other fields related to organic synthesis.1 Introduction2 Chemical Transformations of ESF3 Chemical Transformations of 2-Arylethenesulfonyl Fluorides4 Novel SuFEx Reagents Derived from ESF5 Applications of ESF Derivatives in Medicinal Chemistry6 Applications of ESF Derivatives in Materials Science7 Conclusion

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