Cu(II)-Catalyzed [3+2] Annulation of Thioamides with AIBN: Facile Access to Highly Functionalized Thiazolidine-4-ones

Synthesis ◽  
2021 ◽  
Author(s):  
Pragya Pali ◽  
Dhananjay Yadav ◽  
Gaurav Shukla ◽  
Maya Shankar Singh
Keyword(s):  
Double Bond ◽  
Functional Groups ◽  
Dual Role ◽  
Direct Access ◽  
One Pot ◽  
Simple Method ◽  
Two Component ◽  
Thiazolidine Ring ◽  
Coupling Partner

An efficient and versatile copper-catalyzed unprecedented intermolecular radical [3 + 2] annulation of thioamides with azobisisobutyronitrile (AIBN) is described. This two-component one-pot copper(II)-catalyzed transformation has been achieved via cascade formation of C-S/C−N bonds through the cyclization of in situ generated N,S-acetal intermediate from β-ketothioamide. This operationally simple method allows direct access to synthetically demanding thiazolidin-4-ones in good to excellent yields containing diverse functional groups of different electronic and steric nature. Remarkably, the readily available reaction partners, avoidance of expensive/toxic reagents and the gram scale synthesis are additional attributes to this strategy. AIBN here plays a dual role as radical initiator and unusual source of two carbon coupling partner. Notably, the products possess Z-stereochemistry with regard to the exocyclic C=C double bond at the 2-position of the thiazolidine ring.

A facile and convenient sequential homobimetallic catalytic approach towards β-methylstyrenes. A one-pot Stille cross-coupling/isomerization strategy

2014 ◽  
Vol 12 (22) ◽  
pp. 3735-3743 ◽  
Author(s):  
Sebastián O. Simonetti ◽  
Enrique L. Larghi ◽  
Teodoro S. Kaufman
Keyword(s):  
Double Bond ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
One Pot ◽  
Cross Coupling Reaction

A one-pot approach towards β-methylstyrenes is reported. The transformation involves a Stille cross-coupling reaction of aryl halides with allyltributylstannane, followed by an in situ Pd-catalyzed double bond conjugative migration.

An efficient, room temperature, oxygen radical anion (O2•−) mediated, one-pot, and multicomponent synthesis of spirooxindoles

2017 ◽  
Vol 95 (12) ◽  
pp. 1296-1302 ◽  
Author(s):  
Somaiah Gajaganti ◽  
Shivam Bajpai ◽  
Vandana Srivastava ◽  
Sundaram Singh
Keyword(s):  
Radical Anion ◽  
Room Temperature ◽  
Present Report ◽  
Oxygen Radical ◽  
Direct Access ◽  
Multicomponent Synthesis ◽  
Tetraethylammonium Bromide ◽  
One Pot ◽  
Potassium Superoxide

The present report highlights an efficient use of oxygen radical anion to promote a room temperature multi-component synthesis of spirooxindoles (4a–4l) under mild reaction conditions. The potassium superoxide (KO2) and tetraethylammonium bromide (TEAB) combination generate the oxygen radical anion in situ to promote this transformation. This method offers a sustainable and direct access to the biologically important spirooxindole derivatives in good to excellent yields.

Catalyst and solvent-free alkylation of quinoline N-oxides with olefins: A direct access to quinoline-substituted α-hydroxy carboxylic derivatives

2016 ◽  
Vol 14 (9) ◽  
pp. 2613-2617 ◽  
Author(s):  
Rakesh Kumar ◽  
Inder Kumar ◽  
Ritika Sharma ◽  
Upendra Sharma
Keyword(s):  
Solvent Free ◽  
Direct Access ◽  
One Pot ◽  
Simple Method

A catalyst/solvent-free, one-pot and operationally simple method for the synthesis of quinoline-substituted α-hydroxy carboxylic derivatives by the hydroxyheteroarylation of olefins with quinoline N-oxides is reported.

scholarly journals In Situ g-C3N4@Zno Nanocomposite: One-Pot Hydrothermal Synthesis and Photocatalytic Performance under Visible Light Irradiation

2021 ◽  
Vol 2021 ◽  
pp. 1-10
Author(s):  
Lan Anh Luu Thi ◽  
Mateus Manuel Neto ◽  
Thang Pham Van ◽  
Trung Nguyen Ngoc ◽  
Tuyet Mai Nguyen Thi ◽  
...  
Keyword(s):  
Photocatalytic Activity ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
High Efficiency ◽  
Diffuse Reflectance Spectroscopy ◽  
Light Irradiation ◽  
Nitrate Hexahydrate ◽  
One Pot ◽  
Simple Method

In situ g-C3N4@ZnO nanocomposites (with 0, 1, 3, 5, and 7 wt.% of g-C3N4 in nanocomposite) were synthesized via a one-pot hydrothermal method using precursors of urea, zinc nitrate hexahydrate, and hexamethylenetetramine. The g-C3N4@ZnO nanocomposites were characterized by X-ray diffraction, scanning electron microscope, diffuse reflectance spectroscopy, and photoluminescence spectroscopy. The photocatalyst activity of g-C3N4@ZnO nanocomposites was evaluated via methylene blue degradation experiment under visible light irradiation. The g-C3N4@ZnO nanocomposites showed an enhancement in photocatalytic activity in comparison to pure ZnO which increased with the g-C3N4 content (1, 3, 5, and 7 wt.%) in nanocomposites. The photocatalytic activity reached the highest efficiency of 96.8% when the content of g-C3N4 was 7.0 wt.%. Nanocomposite having 7.0 wt.% of g-C3N4 also showed good recyclability with degradation efficiency higher than 90% even in the 4th use. The improvement of photocatalytic activity could be attributed to the adsorption ability and effective separation of electron-hole pairs between g-C3N4 and ZnO. This work implies a simple method to in situ prepare the nanocomposite material of g-C3N4 and semiconductors oxide for photocatalyst applications with high efficiency and good recyclability.

scholarly journals One-Pot Synthesis of B-Aryl Carboranes with Sensitive Functional Groups Using Sequential Cobalt- and Palladium-Catalyzed Reactions

Catalysts ◽  
2020 ◽  
Vol 10 (11) ◽  
pp. 1348
Author(s):  
Sergey A. Anufriev ◽  
Akim V. Shmal’ko ◽  
Kyrill Yu. Suponitsky ◽  
Igor B. Sivaev
Keyword(s):  
Functional Groups ◽  
X Ray Diffraction ◽  
One Pot ◽  
One Pot Synthesis ◽  
Palladium Catalyzed ◽  
Catalyzed Reactions ◽  
The One ◽  
Solid State Structures ◽  
Derivatives Of

The simple and efficient method was developed for the one-pot synthesis of B-substituted aryl derivatives of ortho-carborane with functional groups sensitive to organolithium and organomagnesium reagents using 9-iodo-ortho-carborane and generated in situ organozinc compounds. The method proposed was used to prepare a series of 9-aryl-ortho-carboranes, including those containing nitrile and ester groups, 9-RC6H4-1,2-C2B10H11 (R = p-Me, p-NMe2, p-OCH2OMe, o-OMe, p-OMe, o-CN, p-CN, o-COOEt, m-COOEt, and p-COOEt). It was demonstrated that the same approach can be used for synthesis of diaryl derivatives of ortho-carborane 9,12-(RC6H4)2-1,2-C2B10H10 (R = H, p-Me). The solid-state structures of 9-RC6H4-1,2-C2B10H11 (R = p-NMe2, p-OCH2OMe, o-OMe, o-CN, p-CN, m-COOEt, and p-COOEt) and 9,12-(p-MeC6H4)2-1,2-C2B10H10 were determined by single crystal X-ray diffraction.

A New Simple Method for the Preparation of Aryl Formates from Phenols

2008 ◽  
Vol 63 (4) ◽  
pp. 478-480 ◽  
Author(s):  
Imran Ali Hashmi ◽  
Willi Kantlehner ◽  
Ivo C. Ivanov
Keyword(s):  
Aluminum Chloride ◽  
One Pot ◽  
Simple Method ◽  
Methanesulfonyl Chloride

AbstractAryl formates are prepared in a two step one-pot procedure from phenols. Firstly the formylating reagent triformamide (1b) is generated from sodium diformamide (2) and methanesulfonyl chloride in situ, which reacts with phenols 4a - f to give aryl formates 5a - f in good yields. Triformamide, prepared in situ, transforms anisole in the presence of aluminum chloride to the N-(diarylmethyl)formamide 7.

scholarly journals One-pot synthesis of GABA amides via the nucleophilic addition of amines to 3,3-disubstituted cyclopropenes

2015 ◽  
Vol 13 (34) ◽  
pp. 8993-8995 ◽  
Author(s):  
Vladimir A. Maslivetc ◽  
Marina Rubina ◽  
Michael Rubin
Keyword(s):  
Double Bond ◽  
Nucleophilic Addition ◽  
Ring Opening ◽  
Secondary Amines ◽  
One Pot ◽  
One Pot Synthesis ◽  
Primary And Secondary Amines ◽  
Donor Acceptor

A one-pot synthesis of various GABA amides has been demostrated, employing the nucleophilic addition of primary and secondary amines across the double bond of cyclopropene-3-carboxamides, followed by ring-opening of the resulting donor–acceptor cyclopropanes and subsequent in situ reduction of enamine intermediates.

scholarly journals Synthesis of 3-Aryl-ortho-carboranes with Sensitive Functional Groups

Molecules ◽  
2021 ◽  
Vol 26 (23) ◽  
pp. 7297
Author(s):  
Sergey A. Anufriev ◽  
Akim V. Shmal’ko ◽  
Kyrill Yu. Suponitsky ◽  
Igor B. Sivaev
Keyword(s):  
Functional Groups ◽  
Intramolecular Hydrogen Bonding ◽  
X Ray Diffraction ◽  
One Pot ◽  
X Ray ◽  
The One ◽  
Intramolecular Hydrogen ◽  
Solid State Structures ◽  
Derivatives Of

A simple and efficient method was developed for the one-pot synthesis of 3-aryl derivatives of ortho-carborane with sensitive functional groups using 3-iodo-ortho-carborane and aryl zinc bromides that were generated in situ. A series of 3-aryl-ortho-carboranes, including those containing nitrile and ester groups, 3-RC6H4-1,2-C2B10H11 (R = p-Me, p-NMe2, p-OCH2OMe, p-OMe, o-CN, p-CN, o-COOEt, m-COOEt, p-COOEt) was synthesized using this approach. The solid-state structures of 3-RC6H4-1,2-C2B10H11 (R = p-OMe, o-CN, and p-CN) were determined by single crystal X-ray diffraction. The intramolecular hydrogen bonding involving the ortho-substituents of the aryl ring and the CH and BH groups of carborane was discussed.

scholarly journals Aqueous Medium Preparation of Dialkyldiselenides

SynOpen ◽  
2018 ◽  
Vol 02 (03) ◽  
pp. 0229-0233 ◽  
Author(s):  
Tapasi Manna ◽  
Anup Misra
Keyword(s):  
Aqueous Medium ◽  
Functional Groups ◽  
Alkaline Hydrolysis ◽  
Alkyl Halides ◽  
Reaction Conditions ◽  
One Pot ◽  
Hydrolysis Of ◽  
Medium Preparation

One-pot, two-step reaction conditions have been developed for the preparation of dialkyl diselenides by the treatment of alkyl halides with potassium selenocyanate followed by alkaline hydrolysis of the in situ generated alkyl selenocyanate in water. The reaction is reasonably fast and the yields of the products were very good. Several functional groups present in the substrates were unaffected under the reaction conditions.

Carbene and Photocatalyst-Catalyzed Decarboxylative Radical Coupling of Carboxylic Acids and Acyl Imidazoles to Form Ketones

2021 ◽  
Author(s):  
Shi-Chao Ren ◽  
Xing Yang ◽  
Bivas Mondal ◽  
Chengli Mou ◽  
Weiyi Tian ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Radical Coupling ◽  
Mild Conditions ◽  
Two Component ◽  
Decarboxylative Coupling ◽  
Coupling Partner ◽  
Powerful Strategy ◽  
Operational Simplicity

Abstract The carbene and photocatalyst co-catalyzed radical coupling of acyl electrophile and a radical precursor is emerging as attractive method for ketone synthesis. However, previous reports mainly limited to prefunctionalized radical precursors and two-component coupling. Herein, an N-heterocyclic carbene and photocatalyst catalyzed decarboxylative radical coupling of carboxylic acids and acyl imidazoles is disclosed, in which the carboxylic acids were directly used as radical precursors. The acyl imidazoles could also be generated in situ by reaction of a carboxylic acid with CDI thus furnishing a formally decarboxylative coupling of two carboxylic acids. In addition, the reaction was successfully extended to three-component coupling by using alkene as a third coupling partner via a radical relay process. The mild conditions, operational simplicity, and use of carboxylic acids as the reacting partners make our method a powerful strategy for construction of complex ketones from readily available starting materials, and late-stage modification of natural products and medicines.

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