Eco-Friendly Methodologies for the Synthesis of Quinoline Nucleus

2019 ◽  
Vol 16 (6) ◽  
pp. 602-608 ◽  
Author(s):  
Ligia S. da Silveira Pinto ◽  
Thatyana R. Alves Vasconcelos ◽  
Marcus V.N. de Souza
Keyword(s):  
Aromatic Compounds ◽  
Reaction Mechanisms ◽  
Reaction Scheme ◽  
Important Class ◽  
Reaction Conditions ◽  
Synthetic Methodologies

The quinoline nucleus is a very important class of heterocyclic aromatic compounds present in several drugs on the market, with synthetic methodologies being necessary to prepare its nucleus and derivatives. Considering that fact, the aim of this review is to describe the development of eco-friendly methodologies for the synthesis of quinoline nucleus and its derivatives in the last five years. Thus, throughout the text are presented varios reagents and catalysts used in the synthesis of quinoline nucleus, the reaction conditions, the advantages of the described methodologies, along with the reaction scheme and some reaction mechanisms.

Recent Advances on Synthesis of 1,4-Benzoxazines and its Derivatives

2021 ◽  
Vol 25 ◽  
Author(s):  
Wei Liang ◽  
Li-Jing Min ◽  
Liang Han ◽  
Xing-Hai Liu
Keyword(s):  
Reaction Mechanisms ◽  
Heterocyclic Compounds ◽  
Synthesis Methods ◽  
Important Class ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Active Structure ◽  
Recent Advances ◽  
The Future

: 1,4-benzoxazine compounds are an important class of heterocyclic compounds. Ever since 1,4-benzoxazine was discovered in 1959, it has attracted chemists due to its unique physiological activities, and their synthesis and application have been studied. However, the traditional synthesis methods of 1,4-benzoxazines have some drawbacks, such as complicated steps, harsh reaction conditions and low yield. Therefore, it is still a significant direction to develop new and efficient synthesis methods. In this paper, the synthesis methods and reaction mechanisms of these compounds are reviewed, and the application prospect of 1,4- benzoxazine and its derivatives as a dominant active structure in the future is discussed.

Synthesis of Phosphonates via Michaelis-Arbuzov Reaction

2017 ◽  
Vol 14 (6) ◽  
pp. 883-903 ◽  
Author(s):  
Boppudi Hari Babu ◽  
Gandavaram Syam Prasad ◽  
Chamarthi Naga Raju ◽  
Mandava Venkata Basaveswara Rao
Keyword(s):  
Reaction Times ◽  
Biologically Active ◽  
Fine Tuning ◽  
Arbuzov Reaction ◽  
Reaction Conditions ◽  
Solvent Type ◽  
Potential Applications ◽  
Synthetic Methodologies ◽  
Optimal Reaction ◽  
The Arbuzov Reaction

Background: Michaelis–Arbuzov reaction has played a key role for the synthesis of dialkyl or diaryl phosphonates by reacting various alkyl or aryl halides with trialkyl or triaryl phosphite. This reaction is very versatile in the formation of P-C bond from the reaction of aliphatic halides with phosphinites or phosphites to yield phosphonates, phosphinates, phosphine oxides. The Arbuzov reaction developed some methodologies, possible mechanistic pathways, selectivity, potential applications and biologically active various phosphonates. Objective: The synthesis of phosphonates via Michaelis–Arbuzov reaction with many new and fascinating methodologies were developed and disclosed in the literature, and these are explored in this review. Conclusion: This review has discussed past developments and vast potential applications of Arbuzov reaction in the synthesis of organophosphonates. As presented in this review, various synthetic methodologies were developed to prepare a large variety of phosphonates. Improvements in the reaction conditions of Lewis-acid mediated Arbuzov rearrangement as well as the development of MW-assisted Arbuzov rearrangement were discussed. Finally, to achieve high selectivities and yields, fine-tuning of reaction conditions including solvent type, temperature, and optimal reaction times to be considered.

C-H bond functionalization using Pd and Au supported catalysts with mechanistic insights of the active species

Synthesis ◽  
2021 ◽  
Author(s):  
Tamao Ishida ◽  
Zhenzhong Zhang ◽  
Haruno Murayama ◽  
Eiji Yamamoto ◽  
Makoto Tokunaga
Keyword(s):  
Aromatic Compounds ◽  
Reaction Mechanisms ◽  
Bond Activation ◽  
Supported Catalysts ◽  
Metal Catalysts ◽  
Active Species ◽  
Supported Metal Catalysts ◽  
Bond Functionalization ◽  
Bond Forming ◽  
Supported Metal

The C–H functionalization has been extensively studied as a direct C–C bond forming reaction with high atomic efficiency. The efforts have also been made on the reaction using supported catalysts, which are superior in terms of catalyst separation from the reaction mixture and reusability. In this review, an overview of the C–H functionalization reactions, especially for Pd and Au supported catalysts will be described. In particular, we discuss reaction mechanisms, active species, leaching, reusability, etc. 1 Introduction 2 Types of supported metal catalysts and their active species 3 Modes of C–H bond activation 4 Oxidative C–H C–H coupling of aryl compounds 5 C–H C–H coupling where one side is aromatic 6 C–H acylation of aromatic compounds and related reactions 7 Conclusion

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 Orthoamide, LXIII [1]. Tris(dichlormethyl)amin, ein neues breit anwendbares Formylierungsmittel für Aromaten / Orthoamides, LXIII [1]. Tris(dichloromethyl)amine, a New Formylating Reagent for Aromatic Compounds of Wide Scope

2006 ◽  
Vol 61 (4) ◽  
pp. 448-463 ◽  
Author(s):  
Willi Kantlehner ◽  
Ralf Kreß ◽  
Franziska Zschach ◽  
Jens Vetter ◽  
Georg Ziegler ◽  
...  
Keyword(s):  
Aluminum Chloride ◽  
Aromatic Compounds ◽  
Lewis Acids ◽  
Aluminium Chloride ◽  
Aromatic Nucleus ◽  
Wide Scope ◽  
Formyl Group ◽  
Reaction Conditions ◽  
Optimal Reaction

The reagent system formed from tris(dichloromethyl)amine (5) and aluminium chloride allows the formylation of aromatic compounds. The scope of the method is comparable with that of the Olah formylation and the Groß-Rieche procedure, since benzene and even chlorobenzene can be formylated. One formyl group is transferred from 5 to the aromatic nucleus. In order to find optimal reaction conditions, the molar amounts of aromatic compounds, 5 and aluminum chloride were varied as well as reaction temperatures and solvents. The activation of 5 with other Lewis acids is also described

Synthesis of Fluorinated Aromatic Compounds by One-Pot Benzyne Generation and Nucleophilic Fluorination

2014 ◽  
Vol 67 (3) ◽  
pp. 475 ◽  
Author(s):  
Takashi Ikawa ◽  
Shigeaki Masuda ◽  
Tsuyoshi Nishiyama ◽  
Akira Takagi ◽  
Shuji Akai
Keyword(s):  
Aromatic Compounds ◽  
Biologically Active ◽  
Reaction Conditions ◽  
Fluoride Ions ◽  
One Pot ◽  
Substituted Benzenes ◽  
Fluorinated Aromatic Compounds ◽  
Nucleophilic Fluorination ◽  
Sequential Reactions

The fluorination of substituted benzenes using fluoride ions under mild reaction conditions has been one of the most important challenges for the synthesis of biologically active fluorinated aromatic compounds; however, only a few synthetically useful methods are known. In this paper, it is reported that the nucleophilic fluorination of benzynes, generated from either 2-(trialkylsilyl)phenyl nonafluorobutanesulfonates or 2-(trialkylsilyl)phenols, meets this challenge. In particular, the fluorination starting from 2-(trialkylsilyl)phenols for fabricating aryl fluorides involves three sequential reactions in one-pot: the nonaflylation of phenols, benzyne generation, and nucleophilic fluorination of the benzynes. The regioselectivities of these reactions are controlled by the substituents at the C3-position of the benzynes.

scholarly journals Topochemical control of the photodimerization of aromatic compounds by γ-cyclodextrin thioethers in aqueous solution

2013 ◽  
Vol 9 ◽  
pp. 1858-1866 ◽  
Author(s):  
Hai Ming Wang ◽  
Gerhard Wenz
Keyword(s):  
Aqueous Solution ◽  
Inclusion Complex ◽  
Aromatic Compounds ◽  
Quantitative Yield ◽  
Quantum Yields ◽  
Reaction Conditions ◽  
Salting Out ◽  
Parallel Orientation

The formation of soluble 1:2 complexes within hydrophilic γ-cyclodextrin (γ-CD) thioethers allows to perform photodimerizations of aromatic guests under controlled, homogenous reaction conditions. The quantum yields for unsubstituted anthracene, acenaphthylene, and coumarin complexed in these γ-CD thioethers were found to be up to 10 times higher than in the non-complexed state. The configuration of the photoproduct reflected the configuration of the dimeric inclusion complex of the guest. Anti-parallel orientation of acenaphthylene within the CD cavity led to the exclusive formation of the anti photo-dimer in quantitative yield. Parallel orientation of coumarin within the complex of a CD thioether led to the formation of the syn head-to-head dimer. The degree of complexation of coumarin could be increased by employing the salting out effect.

THE LUMINOUS MANTLE OF FUEL-RICH OXYACETYLENE FLAMES: II. FREE RADICAL AND CONTINUUM INTENSITIES, AND THEIR INFLUENCE ON C3 EMISSIONS

1957 ◽  
Vol 35 (11) ◽  
pp. 1275-1283 ◽  
Author(s):  
G. V. Marr
Keyword(s):  
Carbon Monoxide ◽  
Free Radical ◽  
Reaction Mechanisms ◽  
Experimental Error ◽  
Carbon Particle ◽  
Black Body ◽  
Reaction Scheme ◽  
Band Head ◽  
Ultraviolet Continuum ◽  
Background Continuum

The spectroscopic emissions from the luminous mantle of the oxyacetylene flame have been examined over a range of burning mixtures from 2.3 to 4.2 times stoichiometric. Plots of the band-head intensities for the radicals C2, C3, CH, and CN for different burning mixtures and for vertical traverses through the flame are reported. From a study of the variation of the background continuum from 3000 Å to 5200 Å with burning mixtures, the over-all continuum may be considered to consist of (a) a black-body carbon particle continuum having an energy distribution corresponding to a temperature of 2900 ± 200° K., (b) a continuum associated with the C3 radical emissions extending from 3500 Å to 4600 Å with a maximum at 4000 Å, and (c) an ultraviolet continuum extending from below 3000 Å to 5000 Å which appears similar to the carbon-monoxide flame continuum. Within the limits of experimental error the variation of the C3 bands and their associated continuum are identical. Possible reaction mechanisms for the production of the C3 emissions are considered and they probably may be accounted for by the reaction scheme[Formula: see text]

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