scholarly journals Orthoamide, LXII [1]. – Mikrowellen-unterst ¨ utzte Formylierung schwach CH2-acider Verbindungen mit dem Bredereck-Simchen Reagenz – Umwandlung der Kondensationsprodukte in Heteroaromaten / Orthoamides, LXII [1]. – Microwave Assisted Formylation of Weak CH2-Acidic Compounds with the Bredereck-Simchen Reagent – Preparation of Heteroaromatic Compounds from the Condensation Products

2005 ◽  
Vol 60 (2) ◽  
pp. 231-241 ◽  
Author(s):  
Willi Kantlehner ◽  
Gerhard Simchen ◽  
Jochen Mezger ◽  
Edmont V. Stoyanov ◽  
Ralf Kreß ◽  
...  
Keyword(s):  
Microwave Irradiation ◽  
Reaction Times ◽  
Conventional Heating ◽  
Methyl Anthranilate ◽  
Prolonged Heating ◽  
Heteroaromatic Compounds ◽  
Microwave Assisted ◽  
Condensation Products ◽  
Acidic Compounds ◽  
Isoxazole Derivatives

The diformylation of the dinitriles 4 and diesters 7 with the Bredereck-Simchen reagent HC[N(CH3)2]2[OC(CH3)3] (1) under microwave irradiation give the bis-enamines 6 and 8 with dramatically reduced reaction times and improved yields compared to conventional heating. The condensation products formed can be easily converted to bis-pyrazole and bis-isoxazole derivatives 13 and 20, respectively. Methyl anthranilate reacts on prolonged heating with the orthoamide 21 to give ketene aminal 23 in low yield (8 %). Under microwave irradiation the same reagents lead to a mixture of 23 (14 %) and dihydropyrane 24 (28 %).

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 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.

Efficient Biginelli Synthesis of 2-Aminodihydropyrimidines under Microwave Irradiation

Synlett ◽  
2018 ◽  
Vol 29 (08) ◽  
pp. 1047-1054 ◽  
Author(s):  
Fulvia Felluga ◽  
Fabio Benedetti ◽  
Federico Berti ◽  
Sara Drioli ◽  
Giorgia Regini
Keyword(s):  
Microwave Irradiation ◽  
Guanidine Hydrochloride ◽  
Reaction Times ◽  
Conventional Heating ◽  
Dicarbonyl Compounds ◽  
Simple Protocol ◽  
Twofold Excess ◽  
General Method

A practical and general method for the Biginelli cyclocondensation of guanidine with aldehydes and β-dicarbonyl compounds is described and illustrated with the synthesis of a set of 26 functionalized 2-amino-3,4-dihydropyrimidines. The simple protocol involves the ­microwave-mediated reaction of a twofold excess of guanidine hydrochloride with the required reaction partners in an alcohol at 120 °C. Yields are generally good, with short reaction times and a simple workup. The scope is considerably wider than that of similar reactions ­carried out under conventional heating.

Improved Protocols for Microwave-Assisted Cu(I)-Catalyzed Huisgen 1,3-Dipolar Cycloadditions

2007 ◽  
Vol 72 (8) ◽  
pp. 1014-1024 ◽  
Author(s):  
Pedro Cintas ◽  
Katia Martina ◽  
Bruna Robaldo ◽  
Davide Garella ◽  
Luisa Boffa ◽  
...  
Keyword(s):  
Heterogeneous Catalysis ◽  
Microwave Irradiation ◽  
Ultrasound Irradiation ◽  
Conventional Heating ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Click Reactions ◽  
Dipolar Cycloadditions ◽  
Microwave Assisted ◽  
New Applications

The Huisgen 1,3-dipolar cycloaddition of azides and acetylenes catalyzed by Cu(I) salts, leading to 1,2,3-triazoles, is one of the most versatile "click reactions". We have developed a series of optimized protocols and new applications of this reaction starting from several substrates, comparing heterogeneous vs homogeneous catalysis, conventional heating vs microwave irradiation or simultaneous microwave/ultrasound irradiation. Both non-conventional techniques strongly promoted the cycloaddition (bromide → azide → triazole), that could be conveniently performed in a one-pot procedure. This was feasible even with such bulky molecules as functionalized β-cyclodextrins (β-CD), starting from 61-O-tosyl-β-CD or from heptakis[6-O-(tert-butyldimethylsilyl)]-21-O-propargyl-β-CD. "Greener" heterogeneous catalysis with charcoal-supported Cu(II) or Cu(I) (prepared under ultrasound) was advantageously employed.

scholarly journals Microwave-assisted modifications of polysaccharides

2014 ◽  
Vol 86 (11) ◽  
pp. 1695-1706 ◽  
Author(s):  
Jacques Desbrières ◽  
Charlotte Petit ◽  
Stéphanie Reynaud
Keyword(s):  
Microwave Irradiation ◽  
High Performance ◽  
Recent Literature ◽  
Conventional Heating ◽  
Natural Polymers ◽  
Environment Friendly ◽  
Microwave Assisted ◽  
The Past ◽  
Energy Consuming

Abstract Polysaccharides are a natural and renewable feed stock for synthesizing high performance macromolecular materials. However, their structure does not allow reaching all properties required for specific applications and chemical modifications are necessary to reach such objectives. Despite the use of natural polymers, the chemistry and processes employed are not environment-friendly due to the nature of chemicals, solvents or because the conventional chemical process are energy-consuming. On the other hand, microwave assisted processes were developed in organic chemistry since the 1980s and more recently for polymer chemistry (polymer formation and modification). Within the chemistry of natural polymers, the use of microwave irradiation has been exploited in the past two decades to alleviate limitations in the synthesis of graft modified polysaccharide materials. Microwave heating is described as more homogeneous, selective and efficient as compared to conventional heating resulting in faster reactions with fewer or no side products as example. Different results reported within the recent literature will be discussed considering the role of microwave irradiation and its consequence on the reaction parameters and properties of final materials. Grafting of polysaccharides, specific modification of polysaccharides or fibers particularly for preparing smart textiles or medical products as well as reactions of polysaccharides to valuable bio-platform molecule will be discussed.

Efficient, microwave-assisted intramolecular 1,3-dipolar cycloadditions of oximes and N-methylnitrones derived from o-alkenylmethoxy-acetophenones

2005 ◽  
Vol 83 (3) ◽  
pp. 260-265 ◽  
Author(s):  
Surinderjit Singh ◽  
M PS Ishar ◽  
Gajendra Singh ◽  
Rajinder Singh
Keyword(s):  
Microwave Irradiation ◽  
Microwave Heating ◽  
Reaction Times ◽  
Solvent Free ◽  
Dipolar Cycloadditions ◽  
Microwave Assisted ◽  
Solvent Free Conditions ◽  
A Minor ◽  
Acetophenone Oxime

Contrary to literature reports, the o-allyloxy- and crotyloxy-acetophenone-oximes (2a, 2b) are transformed to nitrones, which undergo regio- and stereoselective intramolecular 1,3-dipolar cycloadditions, both on microwave heating under solvent free conditions and refluxing in toluene, to afford novel cycloadducts (5a, 5b); the oxazepine-N-oxide (3a) reported to be formed in 98% yield was obtained only as a minor product (~10%). However, o-cinnamyloxy-acetophenone-oxime (2c) under similar conditions undergoes intramolecular N-alkylation to afford nitrone (3c). The reactions carried out under microwave irradiation are cleaner, require shorter reaction times, and have higher yields. Corresponding intramolecular 1,3-dipolar cycloadditions of N-methylnitrones (B), generated in situ from o-alkenylmethoxy-acetophenones (1a–1c) and N-methylhydroxylamine under solvent-free microwave irradiation conditions, are completely regio- and stereoselective, require much shorter reaction times, and afford adducts (4a–4c) in higher yields, as compared with their thermal counterparts.Key words: cycloadditions, nitrones, oximes, o-alkenylmethoxy-acetophenones, microwave, isoxazolidines.

scholarly journals Green, Microwave-Assisted Synthesis of O-Perbutyrylated-Alkyl-Glycosides

Proceedings ◽  
2019 ◽  
Vol 41 (1) ◽  
pp. 42
Author(s):  
Emmanuel Pérez-Escalante ◽  
Luis Guillermo González-Olivares ◽  
Araceli Castañeda-Ovando ◽  
Verónica Salazar-Pereda ◽  
John F. Trant ◽  
...  
Keyword(s):  
Lewis Acids ◽  
Model Compound ◽  
Traditional Approach ◽  
Reaction Times ◽  
Conventional Heating ◽  
Microwave Assisted Synthesis ◽  
Hydroxyl Groups ◽  
Alkyl Glycosides ◽  
Microwave Assisted ◽  
Synthetic Strategy

Chemical synthesis of carbohydrates is a challenging task. Several protection and deprotection steps of hydroxyl groups are required to ensure regioselective formation of the glycosidic bond. Usually, it is achieved through acylation, where conventional heating is combined with addition of Lewis acids as catalysts. This traditional approach has two drawbacks; it is time consuming and often catalysts are hazardous to the environment. An alternative route relies on application of microwaves and/or other Lewis acids with less or no toxicity. Such combination would reduce reaction times and offer a benign synthetic strategy to obtain peracylated compounds. The current work describes an efficient and environmentally mild synthesis of peracylated glycosides with potential application in enzymatic preparation of carbohydrates. Model compound O-perbutyrylated-phenyl-galactose was synthesized using imidazole as catalyst in the microwave-assisted process. The acylation protocol was optimized, and the target sugar was obtained at 50% yield after 1 h. In conclusion, the combination of imidazole and microwaves provides an excellent alternative to swiftly synthesize peracylated glycosides in a benign way.

Microwave-Assisted Synthesis of Azo Aromatic Diacyl Chlorides

2012 ◽  
Vol 524-527 ◽  
pp. 1702-1705
Author(s):  
Qing Chao Jia ◽  
Yan Jun Chen ◽  
Hong Min Hou
Keyword(s):  
Microwave Irradiation ◽  
Ultrasonic Irradiation ◽  
Reaction Times ◽  
Microwave Assisted Synthesis ◽  
Microwave Assisted

Six azo aromatic diacyl chlorides were synthesized under microwave irradiation. The method offers better yields in shorter reaction times compared to classical heating approaches and ultrasonic irradiation.

scholarly journals Microwave-Assisted Synthesis of Arylidene Acetophenones

2013 ◽  
Vol 2013 ◽  
pp. 1-5
Author(s):  
Sheauly Khatun ◽  
M. Z. H. Khan ◽  
Khodeza Khatun ◽  
M. A. Sattar
Keyword(s):  
Microwave Irradiation ◽  
Microwave Heating ◽  
Spectral Data ◽  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
Conventional Heating ◽  
Microwave Assisted Synthesis ◽  
Efficient Synthesis ◽  
H Nmr ◽  
Microwave Assisted

An efficient synthesis of arylidene acetophenones have been achieved by using the microwave heating in comparison to the conventional heating. In this work compound 1-phenyle-3-(4-droxyphenyle)-2-propen-1-one, 1-(4-chlorophenyle)-3-phenyle-2-propen-1-one, and 1-(4-chlorophenyle)-3-(4-hydroxyphenyle)-2-propen-1-one have been synthesized by the condensation reaction between aromatic aldehydes and substituted acetophenones under microwave irradiation. The compounds of aldehydes and acetophenones were used as benzaldehyde, parahydroxybenzaldehyde, acetophenone, and parachloroacetophenone. The result shows that the time taken for the reaction was reduced from the conventional 1-2 hours to 60–120 seconds. The yield of the compounds in the conventional heating was moderate while the highest yield of 90–98% was observed in MWI method. The structure of the compounds was characterized by their IR,1H-NMR spectral data.

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