scholarly journals Sustainable and scalable synthesis of polysubstituted bis-1,2,4-triazoles, bis-2-iminothiazolines and bis-thiobarbiturates using bis-N,N-disubstituted thioureas as versatile substrate

2019 ◽  
Vol 6 (6) ◽  
pp. 181963 ◽  
Author(s):  
Wael Abdelgayed Ahmed Arafa ◽  
Hamada Mohamed Ibrahim
Keyword(s):  
Functional Group ◽  
The Other ◽  
Environmentally Benign ◽  
Reductive Cyclization ◽  
One Pot ◽  
Mild Conditions ◽  
Ring Nitrogen ◽  
Scalable Synthesis ◽  
Operational Simplicity

An expedient and tandem regioselective one-pot protocol for the sono-synthesis of bis-[1,2,4]-triazol-3-yl amines and bis-2-iminothiazolines from corresponding bis-1,3-disubstituted thioureas has been developed. The products' regioselectivity correlate well with the pKas of the parent amines, in which the amine possessing higher pKagoes to the ring nitrogen, whereas the other nitrogen remains flanked as an exocyclic nitrogen of the bis-triazole or bis-thiazole moieties. Further, the sonochemical preparation of both bis-5-(2-nitrobenzylidene) thiobarbiturates and bis-2-thioxoimidazolidine-4,5-diones from bis-1,3-disubstituted thioureas has also been achieved. The obtained bis-5-(2-nitrobenzylidene)thiobarbiturates easily underwent reductive cyclization to afford the corresponding bis-5-benzo[c]isoxazol-3-ylidenethiobarbiturates. The scope and limitations of these strategies have been studied. Moreover, the suggested methodologies have advantages such as broad functional group tolerance, mild conditions, operational simplicity and applicability on a gram scale. Furthermore, the protocols scored well in a number of green metrics, subsequently showing these approaches to be environmentally benign and sustainable processes.

scholarly journals Nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts enabled by NN2 pincer ligand

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Xingjie Zhang ◽  
Di Qi ◽  
Chenchen Jiao ◽  
Xiaopan Liu ◽  
Guisheng Zhang
Keyword(s):  
Functional Group ◽  
High Efficiency ◽  
Materials Science ◽  
Alkylating Agents ◽  
Sonogashira Coupling ◽  
Pincer Ligand ◽  
One Pot ◽  
Mild Conditions ◽  
Alkyl Amines ◽  
Sonogashira Reactions

AbstractAlkynes are amongst the most valuable functional groups in organic chemistry and widely used in chemical biology, pharmacy, and materials science. However, the preparation of alkyl-substituted alkynes still remains elusive. Here, we show a nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts. Key to the success of this coupling is the development of an easily accessible and bench-stable amide-type pincer ligand. This ligand allows naturally abundant alkyl amines as alkylating agents in Sonogashira reactions, and produces diverse alkynes in excellent yields under mild conditions. Salient merits of this chemistry include broad substrate scope and functional group tolerance, gram-scale synthesis, one-pot transformation, versatile late-stage derivatizations as well as the use of inexpensive pre-catalyst and readily available substrates. The high efficiency and strong practicability bode well for the widespread applications of this strategy in constructing functional molecules, materials, and fine chemicals.

Visible-Light-Induced Radical Polynitration of Arylboronic Acids: Synthesis of Polynitrophenols

Synthesis ◽  
2018 ◽  
Vol 50 (15) ◽  
pp. 2891-2896 ◽  
Author(s):  
Jinna Song ◽  
Xihe Bi ◽  
Qi Zhang ◽  
Kaki Raveendra Babu ◽  
Zhouliang Huang
Keyword(s):  
Visible Light ◽  
Aromatic Compounds ◽  
Functional Group ◽  
Simple Procedure ◽  
One Pot ◽  
Arylboronic Acids ◽  
Mild Conditions ◽  
Conventional Methods ◽  
Straightforward Approach

We report a visible light-assisted one-pot method for the synthesis of polynitrophenols through radical tandem hydroxylation and nitration of arylboronic acids by utilizing copper(II) nitrate tri­hydrate as the nitro source. This method features mild conditions, a simple procedure, and good functional group tolerance. Compared to conventional methods, this work provides a straightforward approach for the polynitration of aromatic compounds.

Fe(III)/l-Valine-Catalyzed One-Pot Synthesis of N-Sulfinyl- and N-Sulfonylimines via Oxidative Cascade Reaction of Alcohols with Sulfinamides or Sulfonamides

Synlett ◽  
2018 ◽  
Vol 29 (09) ◽  
pp. 1232-1238
Author(s):  
Guofu Zhang ◽  
Yunzhe Xing ◽  
Shengjun Xu ◽  
Chengrong Ding ◽  
Shang Shan
Keyword(s):  
Catalytic System ◽  
Functional Group ◽  
Cascade Reaction ◽  
One Pot ◽  
Mild Conditions ◽  
One Pot Synthesis ◽  
Oxidation Of Alcohols

An efficient Fe(III), l-valine, and 4-OH-TEMPO catalytic system was found for the oxidation of alcohols followed by condensation with sulfinamide or sulfonamide in one pot for the synthesis of N-sulfinyl- and N-sulfonylimines compounds under mild conditions. This transformation accommodates a variety of substrates, shows high functional-group tolerance, and affords the corresponding products in good to excellent yields.

Efficient Synthesis of Diverse 5-Thio- or 5-Selenotriazoles: One-Pot Multicomponent Reaction from Elemental Sulfur or Selenium

Synthesis ◽  
2019 ◽  
Vol 51 (22) ◽  
pp. 4170-4182 ◽  
Author(s):  
Lin-Lin Zhang ◽  
Ya-Ting Li ◽  
Ting Gao ◽  
Sha-Sha Guo ◽  
Bei Yang ◽  
...  
Keyword(s):  
Elemental Sulfur ◽  
Functional Group ◽  
High Efficiency ◽  
Efficient Synthesis ◽  
One Pot ◽  
Mild Conditions ◽  
Ligand Free ◽  
Multistep Reaction ◽  
Easy Operation

A sequential multistep reaction toward 5-thio- or 5-selenotriazoles has been established by generation of both copper(I) triazolides and sulfenylating or selenylating agents in situ, starting from elemental sulfur or selenium. This reaction features mild conditions, readily available and broad-scope substrates, good functional group compatibility, high efficiency and regioselectivity, easy operation, and ligand-free CuI.

Additive- and Oxidant-Free Expedient Synthesis of Benzimidazoles Catalyzed by Cobalt Nanocomposites on N-Doped Carbon

Synlett ◽  
2019 ◽  
Vol 30 (03) ◽  
pp. 319-324 ◽  
Author(s):  
Zhaozhan Wang ◽  
Tao Song ◽  
Yong Yang
Keyword(s):  
Functional Group ◽  
Direct Synthesis ◽  
Biologically Active ◽  
One Pot ◽  
Mild Conditions ◽  
Wide Range ◽  
High Yields

A one-pot direct synthesis of a wide range of biologically active benzimidazoles through coupling of phenylenediamines and aldehydes catalyzed by a highly recyclable nonnoble cobalt nanocomposite was developed. A broad set of benzimidazoles can be efficiently synthesized in high yields and with good functional-group tolerance under additive- and oxidant-free mild conditions. The catalyst can be easily recycled for successive uses, and the process permits gram-scale syntheses of benzimidazoles.

scholarly journals One-Pot Reductive Acetylation of Aldehydes using 1-Hydrosilatrane in Acetic Acid

SynOpen ◽  
2019 ◽  
Vol 03 (01) ◽  
pp. 1-3 ◽  
Author(s):  
Reuben James ◽  
Sharon Herlugson ◽  
Sami Varjosaari ◽  
Vladislav Skrypai ◽  
Zainab Shakeel ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Organic Synthesis ◽  
Functional Group ◽  
Building Blocks ◽  
Flash Chromatography ◽  
Primary Alcohols ◽  
Facile Synthesis ◽  
One Pot ◽  
Aryl Aldehydes ◽  
Mild Conditions

A one-pot, direct reductive acetylation of aldehydes was achieved under mild conditions using 1-hydrosilatrane as a safe and easily accessible catalyst. Described herein is a facile synthesis that produces acylated primary alcohols that can serve as valuable building blocks for organic synthesis. The method has good functional group tolerance and works for a range of aryl aldehydes, with the notable exception of electron-rich arenes. A library of esters was isolated by flash chromatography in yields as high as 92%.

A one-pot synthesis of tetrazolones from acid chlorides: understanding functional group compatibility, and application to the late-stage functionalization of marketed drugs

2016 ◽  
Vol 14 (39) ◽  
pp. 9338-9342 ◽  
Author(s):  
Matthew A. J. Duncton ◽  
Rajinder Singh
Keyword(s):  
Late Stage ◽  
Functional Group ◽  
Acid Chlorides ◽  
One Pot ◽  
One Pot Synthesis ◽  
Scalable Synthesis

A one-pot and scalable synthesis of tetrazolones (tetrazol-5-ones) from acid chlorides using azidotrimethylsilane is presented.

An ionic liquid catalyzed reusable protocol for one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one under mild conditions

2015 ◽  
Vol 39 (12) ◽  
pp. 9693-9699 ◽  
Author(s):  
S. Nagarajan ◽  
Tanveer Mahamadali Shaikh ◽  
Elango Kandasamy
Keyword(s):  
Ionic Liquid ◽  
Catalytic Activity ◽  
Functional Group ◽  
One Pot ◽  
Mild Conditions ◽  
One Pot Synthesis ◽  
Synthetic Utility

This article describes an efficient protocol for the syntheses of 2,3-dihydroquinazolinones. The synthetic utility of this methodology has been demonstrated with 30 different substrates. The reaction showed good functional group tolerance and high levels of catalytic activity.

Chemoselective Synthesis of N-Arylenaminones and 3-Aroylquinolines by Synergistic Control of Temperature and Amount of Catalyst

Synlett ◽  
2017 ◽  
Vol 29 (04) ◽  
pp. 519-524 ◽  
Author(s):  
Fuchao Yu ◽  
Pan Zhou ◽  
Biao Hu ◽  
Kairui Rao ◽  
Lingdan Li ◽  
...  
Keyword(s):  
Functional Group ◽  
Practical Method ◽  
Mild Conditions ◽  
Toluenesulfonic Acid ◽  
Chemoselective Synthesis ◽  
Operational Simplicity

An efficient and practical method has been developed for the divergent synthesis of N-arylenaminones and 3-aroylquinolines from 2-aminoaryl ketones and N,N-dimethylenaminones in the presence of 4-toluenesulfonic acid through synergistic control of the temperature and amount of catalyst. Furthermore, gram-scale synthesis and synthetic applications have been evaluated. Features of this protocol include controllable results, mild conditions, good functional-group tolerance, operational simplicity, and excellent yields.

scholarly journals FeF3 as a green catalyst for the synthesis of dihydropyrimidines via Biginelli reaction

2020 ◽  
Vol 11 (3) ◽  
pp. 206-212
Author(s):  
Thalishetti Krishna ◽  
Eppakayala Laxminarayana ◽  
Dipak Kalita
Keyword(s):  
Thermal Stability ◽  
Functional Group ◽  
Direct Synthesis ◽  
Biginelli Reaction ◽  
Environmentally Benign ◽  
Green Catalyst ◽  
Mild Conditions ◽  
Highly Efficient ◽  
High Acidity ◽  
Water Tolerance

A facile and highly efficient FeF3-catalyzed method has been developed for the direct synthesis of functionalized dihydropyrimidines from readily available starting materials via Biginelli reaction. These reactions proceed at low-catalyst loadings with high functional group tolerance under mild conditions. This method provides efficient reusability of the catalyst and good to excellent yields of the products, making the protocol more attractive, economical, and environmentally benign. FeF3 is an attractive catalyst for the Biginelli reaction because of its high acidity, thermal stability and water tolerance.

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