Quinoline and phenanthroline preparation starting from glycerol via improved microwave-assisted modified Skraup reaction

RSC Advances ◽  
2014 ◽  
Vol 4 (41) ◽  
pp. 21456-21464 ◽  
Author(s):  
Hanen Saggadi ◽  
Denis Luart ◽  
Nicolas Thiebault ◽  
Isabelle Polaert ◽  
Lionel Estel ◽  
...  
Keyword(s):  
Microwave Irradiation ◽  
Environmentally Friendly ◽  
Microwave Assisted ◽  
Neat Water ◽  
Skraup Reaction

An efficient “green” modified Skraup reaction in neat water was developed using inexpensive, abundant and environmentally-friendly glycerol under microwave irradiation conditions.

Microwave-assisted one-pot syntheses of 4-aminoquinazolines

2016 ◽  
Vol 5 (3) ◽  
Author(s):  
Wenting Song ◽  
Shunli He ◽  
Zeli Yuan ◽  
Guangqing Yu ◽  
Di Wu ◽  
...  
Keyword(s):  
Microwave Irradiation ◽  
Environmentally Friendly ◽  
One Pot ◽  
Microwave Assisted

AbstractA simple, environmentally friendly, one-pot method for the synthesis of 4-aminoquinazolines using microwave irradiation has been developed. Structures of derivatives

scholarly journals Microwave-Assisted Organic Reactions: Eco-friendly Synthesis of Dibenzylidenecyclohexanone Derivatives via Crossed Aldol Condensation

2017 ◽  
Vol 17 (2) ◽  
pp. 336 ◽  
Author(s):  
Sri Handayani ◽  
Cornelia Budimarwanti ◽  
Winarto Haryadi
Keyword(s):  
Optimum Condition ◽  
Microwave Irradiation ◽  
Organic Synthesis ◽  
Aldol Condensation ◽  
Condensation Reaction ◽  
Environmentally Friendly ◽  
Optimum Concentration ◽  
Reaction Yield ◽  
Microwave Assisted ◽  
Benzaldehyde Derivatives

The synthesis of dibenzylidenecyclohexanone derivatives via environmentally friendly Microwave Assisted Organic Synthesis (MAOS) crossed aldol condensation had been carried out. The condensation reaction to synthesize the dibenzylidenecyclohexanone 8b was performed by reacting benzaldehyde 4 and cyclohexanone 2 (mole ratio of 2:1) with NaOH as catalyst for 2 min under microwave irradiation. The benzaldehyde derivatives used in this study were 4-methoxybenzaldehyde and 3,4-dimethoxybenzaldehyde and gave of (2E,6E)-bis(4-methoxy benzylidene)cyclohexanone 8a and (2E,6E)-bis(3,4-dimethoxybenzylidene)cyclohexanone 8c, respectively. The study was commenced by searching the optimum concentration of NaOH. The reaction yield was determined by TLC scanner and the structure was elucidated by FTIR and NMR spectrometers. For the comparison, the reaction was also carried out by using stirring method. The results showed that optimum concentration of NaOH was 5 mmole. By using the optimum condition via MAOS method, the compounds 8a, 8b and 8c were obtained in 100, 98 and 93%, respectively. The research also proved that the method of dibenzylidenecyclohexanones (8) synthesis using MAOS was more efficient than stirring method.

Regioselective Synthesis of Potent 4,5,6,7-Tetrahydroindazole Derivatives via Microwave-assisted Vilsmeier-Haack Reaction and their Antioxidant Activity Evaluation

2019 ◽  
Vol 16 (3) ◽  
pp. 194-201 ◽  
Author(s):  
Renu Bala ◽  
Vandana Devi ◽  
Pratibha Singh ◽  
Navjot Kaur ◽  
Pawandeep Kaur ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Microwave Irradiation ◽  
Biological Activities ◽  
Reaction Times ◽  
Conventional Heating ◽  
High Chemical ◽  
Microwave Assisted ◽  
Work Up ◽  
Active Methylene ◽  
By Products

Background: Tetrahydroindazole, a member of the fused-pyrazole system, is a least studied class of heterocyclic compounds owing to its scarcity in nature. However, a large number of synthetically prepared tetrahydroindazoles are known to show a variety of biological activities such as interleukin- 2 inducible T-Cell kinase inhibitors, AMPA receptor positive allosteric modulators, antitumor, antituberculosis, anti-inflammatory and antimicrobial activities. Vilsmeier-Haack reaction is one of the most important chemical reactions used for formylation of electron rich arenes. Even though Vilsmeier- Haack reaction was studied on a wide variety of hydrazones derived from active methylene compounds, literature lacks the examples of the use of 4-substituted cyclohexanones as a substrate for the synthesis of 4,5,6,7-tetrahydroindazoles. The study of the reaction of Vilsmeier-Haack reagent with hydrazones derived from cyclic keto compounds having active methylene has been considered the interested topic of investigation. In the present study, ethyl cyclohexanone-4-carboxylate was treated with one equivalent of various hydrazines for two hours and the resulted hydrazones were further treated with an OPC-VH reagent (Vilsmeier-Haack reagent isolated from phthaloyl dichloride and N,Ndimethylformamide) afforded 4,5,6,7-tetrahydroindazoles in excellent yields. The synthesized compounds 4a-f and 5a-f were screened for their antioxidant activities using the DPPH radical scavenging assay. The target compounds were synthesized regioselectively using 4+1 approach in excellent yields. A number of experiments using both conventional heating as well as microwave irradiation methods were tried and on comparison, microwave irradiation method was found excellent in terms of easy work up, high chemical yields, shortened reaction times, clean and, no by-products formation. Some of the synthesized compounds showed significant antioxidant activity. The microwave assisted synthesis of 4,5,6,7-tetrahydroindazoles from ethyl cyclohexanone-4-carboxylate has been reported under mild conditions in excellent yield. Easy work up, high chemical yield, shortened reaction times, clean and no by-products formation are the major advantages of this protocol. These advantages may make this method useful for chemists who are interested in developing novel 4,5,6,7-tetrahydroindazole based drugs.

Microwave-assisted Synthesis of Benzoxazoles Derivatives

2020 ◽  
Vol 7 (3) ◽  
pp. 183-195
Author(s):  
Musa Özil ◽  
Emre Menteşe
Keyword(s):  
Microwave Irradiation ◽  
Reaction Medium ◽  
Pharmaceutical Chemistry ◽  
Conventional Heating ◽  
High Yield ◽  
Microwave Assisted Synthesis ◽  
Microwave Assisted ◽  
Optical Brighteners ◽  
Chemistry Research ◽  
Extensive Class

Background: Benzoxazole, containing a 1,3-oxazole system fused with a benzene ring, has a profound effect on medicinal chemistry research owing to its important pharmacological activities. On the other hand, the benzoxazole derivative has exhibited important properties in material science. Especially in recent years, microwave-assisted synthesis is a technique that can be used to increase diversity and quick research in modern chemistry. The utilization of microwave irradiation is beneficial for the synthesis of benzoxazole in recent years. In this focused review, we provide a metaanalysis of studies on benzoxazole in different reaction conditions, catalysts, and starting materials by microwave technique so far, which is different from conventional heating. Methods: Synthesis of different kind of benzoxazole derivatives have been carried out by microwave irradiation. The most used method to obtain benzoxazoles is the condensation of 2-aminophenol or its derivatives with aldehydes, carboxylic acids, nitriles, isocyanates, and aliphatic amines. Results: Benzoxazole system and its derivatives have exhibited a broad range of pharmacological properties. Thus, many scientists have remarked on the importance of the synthesis of different benzoxazole derivatives. Conventional heating is a relatively inefficient and slow method to convey energy in orientation to the reaction medium. However, the microwave-assisted heating technique is a more effective interior heating by straight coupling of microwave energy with the molecules. Conclusion: In this review, different studies were presented on the recent details accessible in the microwave- assisted techniques on the synthesis of the benzoxazole ring. It presents all examples of such compounds that have been reported from 1996 to the present. Benzoxazoles showed an extensive class of chemical substances not only in pharmaceutical chemistry but also in dyestuff, polymer industries, agrochemical, and optical brighteners. Thus the development of fast and efficient achievement of benzoxazoles with a diversity of substituents in high yield is getting more noteworthy. As shown in this review, microwave-assisted synthesis of benzoxazoles is a very effective and useful technique.

scholarly journals Environmentally Friendly Nafion-Catalyzed Synthesis of Substituted 2-Ethyl-3-Methylquinolines from Aniline and Propionaldehyde under Microwave Irradiation

Catalysts ◽  
2021 ◽  
Vol 11 (8) ◽  
pp. 877
Author(s):  
Chieh-Kai Chan ◽  
Chien-Yu Lai ◽  
Cheng-Chung Wang
Keyword(s):  
Reaction Mechanism ◽  
Microwave Irradiation ◽  
Single Crystal ◽  
Diffraction Analysis ◽  
Environmentally Friendly ◽  
Single Crystal Diffraction ◽  
X Ray ◽  
Related Data ◽  
Heating Source ◽  
Chemical Structures

Herein, we report a facile synthetic methodology for the preparation of 2,3-dialkylquinolines from anilines and propionaldehydes. This cyclization involved environmentally friendly Nafion® NR50 as an acidic catalyst with microwave irradiation as the heating source. A series of substituted 2-ethyl-3-methylquinolines were prepared from various anilines and propionaldehyde derivatives through this protocol with good to excellent yields. Some new chemical structures were confirmed by X-ray single-crystal diffraction analysis and the related data were provided. The plausible reaction mechanism studies are also discussed.

scholarly journals Microwave-Assisted Asinger Synthesis of Thiazolines

2020 ◽  
Vol 3 (1) ◽  
pp. 27
Author(s):  
Raúl Eduardo Gordillo-Cruz ◽  
Liliana Gonzalez-Reyes ◽  
Milton Coporo-Reyes ◽  
Nieves Zavala-Segovia ◽  
Bernardo A. Frontana-Uribe ◽  
...  
Keyword(s):  
Microwave Irradiation ◽  
Reaction Times ◽  
Reaction Conditions ◽  
Microwave Assisted

An array of 2,4-disubstituted thiazolines was obtained through Asinger reaction approach from the straightforward treatment of diverse aldehydes/ketones with 1-mercaptopropan-2-one, in the presence of NH3 assisted by microwave irradiation, displaying similar and sometimes higher yields, as well as shorter reaction times that traditional Asinger reaction conditions at room and lower temperatures.

scholarly journals Cycloaddition of Thiourea- and Guanidine-Substituted Furans to Dienophiles: A Comparison of the Environmentally-Friendly Methods

2020 ◽  
Vol 3 (1) ◽  
pp. 57
Author(s):  
Luka Barešić ◽  
Davor Margetić ◽  
Zoran Glasovac
Keyword(s):  
High Pressure ◽  
Functional Groups ◽  
Organic Synthesis ◽  
High Speed ◽  
Environmentally Friendly ◽  
Microwave Assisted ◽  
Pressure Synthesis ◽  
Ultrasound Assisted ◽  
Substituted Furans ◽  
Guanidine Moiety

The cycloaddition strategy was employed in order to obtain a 7-oxanorbornene framework substituted with a guanidine moiety or its precursor functional groups: protected amine or thiourea. In order to optimize the conditions for the cycloaddition, several environmentally-friendly methods—microwave assisted organic synthesis, high pressure synthesis, high speed vibrational milling, and ultrasound assisted synthesis—were employed. The outcomes of the cycloaddition reactions were interpreted in terms of endo/exo selectivity, the conversion of the reactants to the product, and the isolated yields. In general, our results indicated the HP and HSVM approaches as the methods of choice to give good yields and conversions.

scholarly journals Microwave-assisted Oxidation of Alcohols by Pyridinium Chlorochromate

1999 ◽  
Vol 23 (2) ◽  
pp. 118-119
Author(s):  
Vaishali Chakraborty ◽  
Manobjyoti Bordoloi
Keyword(s):  
Microwave Irradiation ◽  
Pyridinium Chlorochromate ◽  
Microwave Assisted ◽  
Oxidation Of Alcohols

An efficient and mild methodology for the oxidation of alcohols to the corresponding carbonyl functions is described using pyridinium chlorochromate under microwave irradiation.

Silk degumming using microwave irradiation as an environmentally friendly surface modification method

2010 ◽  
Vol 11 (2) ◽  
pp. 234-240 ◽  
Author(s):  
Niyaz Mohammad Mahmoodi ◽  
Fereshteh Moghimi ◽  
Mokhtar Arami ◽  
Firoozmehr Mazaheri
Keyword(s):  
Surface Modification ◽  
Microwave Irradiation ◽  
Environmentally Friendly ◽  
Modification Method

Microwave-assisted synthesis of quinolones and 4H-1,4-benzo thiazine 1,1-dioxides

2005 ◽  
Vol 2005 (1) ◽  
pp. 27-28 ◽  
Author(s):  
Jaime Charris ◽  
Arthur Barazarte ◽  
José Domínguez ◽  
Neira Gamboa
Keyword(s):  
Microwave Irradiation ◽  
Rapid Method ◽  
Solvent Free ◽  
Microwave Assisted Synthesis ◽  
Microwave Assisted ◽  
Solvent Free Conditions

A rapid method for the preparation of N-aryl-2-methylthio-4-oxo-1,4-dihydro quinoline-3-carbonitriles (2a–e) and N-aryl-3-methylthio-4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxides (2f–o) is reported. The cyclization is accelerated by microwave irradiation under solvent free conditions in the presence of K2CO3.

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