N-Acylation of Oxazolidinones via Aerobic Oxidative NHC Catalysis

2018 ◽  
Author(s):  
Linda Ta ◽  
Anton Axelsson ◽  
Henrik Sundén
Keyword(s):  
Green Chemistry ◽  
Room Temperature ◽  
Functional Group ◽  
Alternative Methods ◽  
Waste Prevention ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Separate Activation ◽  
Reaction Vessels ◽  
Acylation Reactions

<p>In the ongoing quest to find alternatives to atom un-economical and forcing conditions in acylation reactions, aerobic oxidative NHC catalysis has emerged as a method to convert aldehydes to potent acylating reagents. This strategy has been utilized in the esterification of alcohols but not yet been shown for densely polyfunctionalized <i>N</i>- heterocycles such as, oxazolidinones and pyrrolidinones. Conventional acylation of oxazolidinones are typically associated with forcing reaction conditions, requiring separate activation steps and strong bases, which does not adhere to the principles of green chemistry. For reasons of waste prevention, atom economy, less hazardous syntheses and reduction of derivatives finding alternative methods are desirable.</p><p> </p>In this manuscript, we demonstrate the synthesis of several <i>N</i>-acylated oxazolidinones and pyrrolidinones that are chemically relevant, both found as pharmaceuticals and natural products as well as auxiliaries for synthesis. The developed method operates at room temperature and can be performed in ethyl acetate with open reaction vessels. The substrate scope is broad, with products isolated in good to excellent yields. The functional group tolerance is exemplified with 22 entries, where different aldehydes, oxazolidinones and pyrrolidinones are systematically investigated. Moreover, the reaction is clean as water is generated as the only byproduct.

N-Acylation of Oxazolidinones via Aerobic Oxidative NHC Catalysis

2018 ◽  
Author(s):  
Linda Ta ◽  
Anton Axelsson ◽  
Henrik Sundén
Keyword(s):  
Green Chemistry ◽  
Room Temperature ◽  
Functional Group ◽  
Alternative Methods ◽  
Waste Prevention ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Separate Activation ◽  
Reaction Vessels ◽  
Acylation Reactions

<p>In the ongoing quest to find alternatives to atom un-economical and forcing conditions in acylation reactions, aerobic oxidative NHC catalysis has emerged as a method to convert aldehydes to potent acylating reagents. This strategy has been utilized in the esterification of alcohols but not yet been shown for densely polyfunctionalized <i>N</i>- heterocycles such as, oxazolidinones and pyrrolidinones. Conventional acylation of oxazolidinones are typically associated with forcing reaction conditions, requiring separate activation steps and strong bases, which does not adhere to the principles of green chemistry. For reasons of waste prevention, atom economy, less hazardous syntheses and reduction of derivatives finding alternative methods are desirable.</p><p> </p>In this manuscript, we demonstrate the synthesis of several <i>N</i>-acylated oxazolidinones and pyrrolidinones that are chemically relevant, both found as pharmaceuticals and natural products as well as auxiliaries for synthesis. The developed method operates at room temperature and can be performed in ethyl acetate with open reaction vessels. The substrate scope is broad, with products isolated in good to excellent yields. The functional group tolerance is exemplified with 22 entries, where different aldehydes, oxazolidinones and pyrrolidinones are systematically investigated. Moreover, the reaction is clean as water is generated as the only byproduct.

Rh(III)-Catalyzed Olefination and Alkylation of Arenes with Maleimides: A Tunable Strategy for C(sp2)–H Functionalization

Synthesis ◽  
2021 ◽  
Author(s):  
Hongji Li ◽  
Wenjie Zhang ◽  
Xueyan Liu ◽  
Zhenfeng Tian
Keyword(s):  
Room Temperature ◽  
Functional Group ◽  
Reaction Conditions ◽  
Bond Functionalization ◽  
Alkylation Process ◽  
Coupling Partner

AbstractWe herein report a new nitrogen-directed Rh(III)-catalyzed C(sp2)–H bond functionalization of N-nitrosoanilines and azoxybenzenes with maleimides as a coupling partner, in which the olefination/alkylation process can be finely controlled at room temperature by variation of the reaction conditions. This method shows excellent functional group tolerance, and presents a mild access to the resulting olefination/alkylation products in moderate to good yields.

scholarly journals Efficient synthesis of pyrazolopyridines containing a chromane backbone through domino reaction

2019 ◽  
Vol 15 ◽  
pp. 874-880
Author(s):  
Razieh Navari ◽  
Saeed Balalaie ◽  
Saber Mehrparvar ◽  
Fatemeh Darvish ◽  
Frank Rominger ◽  
...  
Keyword(s):  
Room Temperature ◽  
High Selectivity ◽  
Domino Reaction ◽  
Primary Amines ◽  
Efficient Synthesis ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Efficient Approach ◽  
Three Component Reaction ◽  
High Yields

An efficient approach for the synthesis of pyrazolopyridines containing the aminochromane motif through a base-catalyzed cyclization reaction is reported. The synthesis was carried out through a three-component reaction of (arylhydrazono)methyl-4H-chromen-4-one, malononitrile, primary amines in the presence of Et3N at room temperature. However, carrying out the reaction under the same conditions without base led to a fused chromanyl-cyanopyridine. High selectivity, high atom economy, and good to high yields in addition to mild reaction conditions are the advantages of this approach.

scholarly journals Can Green Synthesis of Nanoparticles be Efficient all Year Long?

2019 ◽  
pp. 32-36
Author(s):  
Mayara Santana dos Santos ◽  
Otávio Augusto Leitão dos Santos ◽  
Sérgio Antunes Filho ◽  
Julia Corrêa dos Santos Santana ◽  
Felipe Motta de Souza ◽  
...  
Keyword(s):  
Energy Efficiency ◽  
Green Synthesis ◽  
Waste Prevention ◽  
Atom Economy ◽  
Green Technologies ◽  
Reaction Conditions ◽  
Synthesis Of Nanoparticles ◽  
Nanomaterial Synthesis ◽  
Low Toxicity ◽  
Synthesis Routes

In recent years, the search for inexpensive and eco-friendly synthesis routes has increased significantly. Nanotechnology and biotechnology have established themselves as a major ally in building green technologies for effective, stable, and non-toxic nanomaterial synthesis. [1-3]. Thus, the principles of green bio nanotechnology are associated with waste prevention, maximizing atom economy, and less use of precursors with less hazardous synthesis routes and the use of safe chemicals with low toxicity. Reaction conditions are also advantageous due to safe methodologies and increased energy efficiency.

Copper(I)-Catalyzed Sulfenylation of 1,3-Dicarbonyl Substrates with Disulfides under Mild Conditions

Synlett ◽  
2019 ◽  
Vol 30 (19) ◽  
pp. 2181-2184 ◽  
Author(s):  
Jingnan Zhao ◽  
Fan Yang ◽  
Zongyi Yu ◽  
Xiaofei Tang ◽  
Yufeng Wu ◽  
...  
Keyword(s):  
Functional Group ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Keto Esters ◽  
Mild Conditions ◽  
Easy Operation

A copper(I) iodine catalyzed sulfenylation of 1,3-dicarbonyl substrates in the presence of MeCN is presented. Various β-keto esters and β-keto amide substrates can react with disulfides to afford their corresponding products in good to excellent yields. The notable features of this protocol include high atom economy, easy operation, mild reaction conditions, and excellent functional group tolerance.

Mandelic acid: An efficient organo-catalyst for the synthesis of 3-substituted- 3-hydroxy-indolin-2-ones and related derivatives in aqueous ethanol at room temperature

2020 ◽  
Vol 07 ◽  
Author(s):  
Gurpreet Kaur ◽  
Rajat Kumar ◽  
Shivam Saroch ◽  
Vivek Kumar Gupta ◽  
Bubun Banerjee
Keyword(s):  
Mandelic Acid ◽  
Room Temperature ◽  
Aqueous Ethanol ◽  
Catalytic Amount ◽  
Environmentally Benign ◽  
Scale Production ◽  
Indole Derivatives ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Naturally Occurring

Background: Indoles and various indolyl derivates are very common in naturally occurring biological active compounds. Many methods are being developed for the synthesis of various bioactive indole derivatives. Objective: Synthesis of biologically promising structurally diverse indole derivatives under mild and environmentally benign conditions. Methods: Synthesis of 3-hydroxy-3-(5-(trifluoromethoxy)-1H-indol-3-yl)indolin-2-one was achieved by the reaction of equimolar mixture of isatin and 3-(trifluoromethoxy)-1H-indol using 20 mol% of mandelic acid as catalyst in aqueous ethanol at room temperature. Under the same optimized reaction conditions, synthesis of 3-(3-hydroxy-2-oxoindolin-3- yl)chroman-2,4-diones was accomplished via the reactions of substituted isatins and 4-hydroxycoumarin. On the other hand, 2-hydroxy-2-(indol-3-yl)-indene-1,3-diones and 10-hydroxy-10-(5-methoxy-1H-indol-3-yl)phenanthren-9(10H)-one were synthesized from the reactions of indoles and ninhydrin or 9,10-phenanthrenequinone respectively using the same 20 mol% of mandelic acid as an efficient organo-catalyst in aqueous ethanol at room temperature. Results: Mild, safe and clean reaction profiles, energy efficiency, high atom-economy, use of naturally occurring nontoxic organo-catalyst, easy isolation procedure by avoiding column chromatographic purification and gram scale production are some the major advantages of this developed protocol. Conclusion: A simple, straightforward and eco-friendly protocol has been developed for the efficient synthesis of biologically promising novel 3-hydroxy-3-(5-(trifluoromethoxy)-1H-indol-3-yl)indolin-2-one, 3-(3-hydroxy-2- oxoindolin-3-yl)chroman-2,4-diones, 2-hydroxy-2-(indol-3-yl)-indene-1,3-diones and 10-hydroxy-10-(5-methoxy-1Hindol-3-yl)phenanthren-9(10H)-one using a catalytic amount of mandelic acid in aqueous ethanol at room temperature.

Microwave Induced Green chemistry approach towards synthesis of heterocyclic compounds via C-N Bond Forming Reactions

2021 ◽  
Vol 08 ◽  
Author(s):  
Bimal Krishna Banik ◽  
Biswa Mohan Sahoo ◽  
BVV Ravi Kumar ◽  
Krishna Chandra Panda
Keyword(s):  
Green Chemistry ◽  
Ring Opening ◽  
Heterocyclic Compounds ◽  
Unique Feature ◽  
Ring Closure ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Formation Reaction ◽  
Bond Forming ◽  
Bond Forming Reactions

: The synthesis of heterocyclic compounds via carbon-nitrogen (C-N) bond formation reaction is considered as an emerged and efficient protocol in the field of synthetic chemistry. The C–N bond-forming reactions can proceed through condensation, coupling, ring-opening, cyclization or ring closure process etc. The reactivity pattern of these reactions mainly depends upon the reaction conditions as well as the type of catalysts and reacting substances that are associated with the synthesis of heterocyclic compounds containing the C-N system including pyrazole, imidazole, pyridine, pyrimidine, thiazole, tetrazole, isoxazole, benzothiazine and benzimidazole etc. Further, the technique of microwave-induced synthesis becomes an alternative strategy for the sustainable production of structurally diverse organic compounds. This method provides a cleaner reaction, faster reaction rate, atom economy and energy-efficient. So, the utilization of microwave radiation in organic synthesis becomes resource-friendly and eco-friendly processes. It follows the green chemistry approach by using safer solvents, renewable starting materials and green catalysts. The unique feature of this method is to generate various types of bioactive or medicinal agents.

Carbohydrate protein interactions. Syntheses of agglutination inhibitors of wheat germ agglutinin by phase transfer catalysis

1991 ◽  
Vol 69 (5) ◽  
pp. 817-821 ◽  
Author(s):  
René Roy ◽  
François D. Tropper
Keyword(s):  
Protein Interactions ◽  
Wheat Germ ◽  
Room Temperature ◽  
Functional Group ◽  
Phase Transfer Catalysis ◽  
Methylene Chloride ◽  
Phase Transfer ◽  
Hydrogen Sulfate ◽  
Reaction Conditions ◽  
Tetrabutylammonium Hydrogen Sulfate

Starting from chloride 1, a series of para-substituted aryl 2-acetamido-2-deoxy-β-D-glucopyranosides were prepared using phase transfer catalysis conditions with tetrabutylammonium hydrogen sulfate in 1 M sodium hydroxide and methylene chloride at room temperature. Zemplén de-O-acetylation afforded the unprotected glycosides. Optimization of reaction conditions was evaluated. Several functional group manipulations were effected to widen the number and nature of the para-substituents. Key words: phase transfer catalysis, aryl 2-acetamido-2-deoxy-β-D-glucopyranosides.

Naturally Occurring Organic Acid-catalyzed Facile Diastereoselective Synthesis of Biologically Active (E)-3-(arylimino)indolin-2-one Derivatives in Water at Room Temperature

2019 ◽  
Vol 23 (16) ◽  
pp. 1778-1788 ◽  
Author(s):  
Gurpreet Kaur ◽  
Arvind Singh ◽  
Kiran Bala ◽  
Mamta Devi ◽  
Anjana Kumari ◽  
...  
Keyword(s):  
Room Temperature ◽  
Biologically Active ◽  
Environmentally Benign ◽  
Diastereoselective Synthesis ◽  
Substituted Anilines ◽  
Reaction Conditions ◽  
Naturally Occurring ◽  
Acid Catalyzed ◽  
Reaction Media ◽  
Column Chromatographic

A simple, straightforward and efficient method has been developed for the synthesis of (E)-3-(arylimino)indolin-2-one derivatives and (E)-2-((4-methoxyphenyl)imino)- acenaphthylen-1(2H)-one. The synthesis of these biologically-significant scaffolds was achieved from the reactions of various substituted anilines and isatins or acenaphthaquinone, respectively, using commercially available, environmentally benign and naturally occurring organic acids such as mandelic acid or itaconic acid as catalyst in aqueous medium at room temperature. Mild reaction conditions, energy efficiency, good to excellent yields, environmentally benign conditions, easy isolation of products, no need of column chromatographic separation and the reusability of reaction media are some of the significant features of the present protocol.

A Facile, Efficient and Selective Deprotection of P - Methoxy Benzyl Ethers Using Zinc (II) Trifluoromethanesulfonate

2019 ◽  
Vol 16 (12) ◽  
pp. 955-958
Author(s):  
Reddymasu Sireesha ◽  
Reddymasu Sreenivasulu ◽  
Choragudi Chandrasekhar ◽  
Mannam Subba Rao
Keyword(s):  
Room Temperature ◽  
Protecting Groups ◽  
Side Reactions ◽  
Reaction Conditions ◽  
Acid Sensitivity ◽  
Time Period ◽  
Protective Groups ◽  
Benzyl Ethers ◽  
Last Stage ◽  
Zinc Triflate

: Deprotection is significant and conducted over mild reaction conditions, in order to restrict any more side reactions with sensitive functional groups as well as racemization or epimerization of stereo center because the protective groups are often cleaved at last stage in the synthesis. P - Methoxy benzyl (PMB) ether appears unique due to its easy introduction and removal than the other benzyl ether protecting groups. A facile, efficient and highly selective cleavage of P - methoxy benzyl ethers was reported by using 20 mole% Zinc (II) Trifluoromethanesulfonate at room temperature in acetonitrile solvent over 15-120 min. time period. To study the generality of this methodology, several PMB ethers were prepared from a variety of substrates having different protecting groups and subjected to deprotection of PMB ethers using Zn(OTf)2 in acetonitrile. In this methodology, zinc triflate cleaves only PMB ethers without affecting acid sensitivity, base sensitivity and also chiral epoxide groups.

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