scholarly journals Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis

2018 ◽  
Vol 14 ◽  
pp. 1508-1528 ◽  
Author(s):  
Gwendal Grelier ◽  
Benjamin Darses ◽  
Philippe Dauban
Keyword(s):  
Nucleophilic Addition ◽  
Coupling Reaction ◽  
Building Blocks ◽  
Tandem Reactions ◽  
Atom Economy ◽  
One Pot

Most of the polyvalent organoiodine compounds derive from iodoarenes, which are released in stoichiometric amounts in any reaction mediated by λ3- or λ5-iodanes. In parallel to the development of solid-supported reagents or reactions catalytic in iodine, a third strategy has emerged to address this issue in terms of sustainability. The atom-economy of transformations involving stoichiometric amounts of λ3- or λ5-iodanes, thus, has been improved by designing tandem reactions that allows for incorporating the aryl motif into the products through a subsequent one-pot nucleophilic addition or catalytic coupling reaction. This review summarizes the main achievements reported in this area.

A Novel, Fast and Efficient One-Pot Three-Component Procedure for the Preparation of New Imidazolidinone Derivatives from Isocyanide, Aldehyde and Urea

2019 ◽  
Vol 21 (9) ◽  
pp. 646-651
Author(s):  
Hamidreza Safaei ◽  
Neda Firoozi ◽  
Mahboobeh Zebarjadian ◽  
Seyed Ali Jehbez ◽  
Maryam Safaei
Keyword(s):  
Green Chemistry ◽  
Ammonium Chloride ◽  
Good Yield ◽  
Building Blocks ◽  
Inorganic Compound ◽  
Automated Synthesis ◽  
Complex Structures ◽  
Atom Economy ◽  
One Pot ◽  
Straightforward Method

Background: Multicomponent processes have played powerful roles in achieving complex structures, which are also aligned with green chemistry. Thus, MCRs have attracted considerable interest due to their atom economy, simple experimental procedures, automated synthesis, convenience and synthetic efficiency. Isocyanides are one of the crucial starting material in designing MCRs methods. They are unique building blocks in many cycloaddition reactions since they are able to react with both nucleophiles and electrophiles at the same carbon. Furthermore, ammonium chloride is an inorganic compound that is highly soluble in water, inexpensive and commercially available. Solutions of ammonium chloride are mildly acidic and have been used in various reactions. Objective: This article focuses on design a convenient and straightforward method for assembling important scaffolds such imidazolidinones through one-pot three-component strategy. Conclusion: The straightforward and efficient one-pot three component method for the synthesis of 4-(cyclohexylmethylene)-5-phenylimidazolidin-2-one derivatives is described. This reaction exploits the formation of imine, which undergoes spontaneous intermolecular cycloaddition with isocyanide, and generates the desired products in a good yield.

Asymmetric tandem reactions: New synthetic strategies

2010 ◽  
Vol 82 (3) ◽  
pp. 669-677 ◽  
Author(s):  
Santos Fustero ◽  
María Sánchez-Roselló ◽  
Carlos del Pozo
Keyword(s):  
Nucleophilic Addition ◽  
Multicomponent Reactions ◽  
Tandem Reactions ◽  
Aromatic Substitution ◽  
Atom Economy ◽  
Complex Molecules ◽  
Cross Metathesis ◽  
Carbonyl Derivatives ◽  
Synthetic Sequence ◽  
First Time

The use of domino and multicomponent reactions in asymmetric synthesis is constantly increasing nowadays. This allows for the synthesis of complex molecules in a single synthetic sequence, usually with high atom economy. Herein, we report three examples of new asymmetric tandem reactions recently developed in our laboratories, giving rise to new families of enantiomerically enriched fluorinated and nonfluorinated heterocycles. Thus, 1,4-dihydropyridines (1,4-DHPs) bearing fluorinated substituents at C6 were assembled by means of a Hantzsch-type reaction; cyclic β-amino carbonyl derivatives were prepared using a cross-metathesis (CM)–intramolecular aza-Michael sequence; while fluorinated indolines were obtained, for the first time, in a tandem nucleophilic addition–intramolecular aromatic substitution.

scholarly journals Modern Approaches to the Synthesis and Transformations of Practically Valuable Benzothiazole Derivatives

Molecules ◽  
2021 ◽  
Vol 26 (8) ◽  
pp. 2190
Author(s):  
Larisa V. Zhilitskaya ◽  
Bagrat A. Shainyan ◽  
Nina O. Yarosh
Keyword(s):  
Green Chemistry ◽  
Building Blocks ◽  
Biologically Active ◽  
New Drugs ◽  
Synthesis Methods ◽  
Atom Economy ◽  
One Pot ◽  
Benzothiazole Derivatives ◽  
Pharmacologically Active ◽  
Synthetic Approaches

The review is devoted to modern trends in the chemistry of 2-amino and 2-mercapto substituted benzothiazoles covering the literature since 2015. The reviewed heterocycles belong to biologically active and industrially demanded compounds. Newly developed synthesis methods can be divided into conventional multistep processes and one-pot, atom economy procedures, realized using green chemistry principles and simple reagents. The easy functionalization of the 2-NH2 and 2-SH groups and the benzene ring of the benzothiazole moiety allows considering them as highly reactive building blocks for organic and organoelement synthesis, including the synthesis of pharmacologically active heterocycles. The review provides a summary of findings, which may be useful for developing new drugs and materials and new synthetic approaches and patterns of reactivity.

scholarly journals Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction

2011 ◽  
Vol 7 ◽  
pp. 1570-1576 ◽  
Author(s):  
Elizabeth P Jones ◽  
Peter Jones ◽  
Andrew J P White ◽  
Anthony G M Barrett
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Nucleophilic Addition ◽  
Ring Opening ◽  
Coupling Reaction ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Aryl Group ◽  
Hydrolysis Of

A method was developed for the synthesis of α-alkyl, α-aryl-bislactim ethers in good to excellent yields and high diastereoselectivities, consisting of a facile one-pot procedure in which the aryl group is introduced by means of a nucleophilic addition to benzyne and the alkyl group by alkylation of a resultant benzylic anion. Hydrolysis of the sterically less hindered adducts gave the corresponding quaternary amino acids with no racemization, whereas hydrolytic ring opening gave the corresponding valine dipeptides from bulkier bislactims.

Insulating Composites Made from Sulfur, Canola Oil, and Wool

2020 ◽  
Author(s):  
Israa Bu Najmah ◽  
Nicholas Lundquist ◽  
Melissa K. Stanfield ◽  
Filip Stojcevski ◽  
Jonathan A. Campbell ◽  
...  
Keyword(s):  
Tensile Strength ◽  
Canola Oil ◽  
Building Blocks ◽  
Atom Economy ◽  
Flame Resistance ◽  
Sustainable Building ◽  
Second Stage ◽  
Wool Fibers ◽  
Insulating Properties ◽  
Polysulfide Polymer

An insulating composite was made from the sustainable building blocks wool, sulfur, and canola oil. In the first stage of the synthesis, inverse vulcanization was used to make a polysulfide polymer from the canola oil triglyceride and sulfur. This polymerization benefits from complete atom economy. In the second stage, the powdered polymer is mixed with wool, coating the fibers through electrostatic attraction. The polymer and wool mixture is then compressed with mild heating to provoke S-S metathesis in the polymer, which locks the wool in the polymer matrix. The wool fibers impart tensile strength, insulating properties, and flame resistance to the composite. All building blocks are sustainable or derived from waste and the composite is a promising lead on next-generation insulation for energy conservation.

Synthesis of Nitrile-Bearing Quaternary Centers via an Equilibrium-Driven Transnitrilation and Anion-Relay Strategy

2019 ◽  
Author(s):  
Sebastien Alazet ◽  
Michael West ◽  
Purvish Patel ◽  
Sophie Rousseaux
Keyword(s):  
Building Blocks ◽  
One Pot ◽  
Quaternary Centers ◽  
Synthetic Intermediates

The efficient preparation of nitrile-containing building blocks is of interest due to their utility as synthetic intermediates and their prevalence in pharmaceuticals. As a result, significant efforts have been made to develop methods to access these motifs which rely on safer and non-toxic sources of CN. Herein, we report that 2-methyl-2-phenylpropanenitrile is an efficient, non-toxic, electrophilic CN source for the synthesis of nitrile-bearing quaternary centers via a thermodynamic transnitrilation and anion-relay strategy. This one-pot process leads to nitrile products resulting from the gem-difunctionalization of alkyl lithium reagents.<br>

Novel One-pot Synthesis of Pyranocarbazole Derivatives via an Isocyanide-based Three-component Reaction

2020 ◽  
Vol 17 ◽  
Author(s):  
Visarapu Malathi ◽  
Pedavenkatagari Narayana Reddy ◽  
Pannala Padmaja
Keyword(s):  
Efficient Method ◽  
Atom Economy ◽  
Reaction Conditions ◽  
One Pot ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
High Yields

Abstract:: An efficient method has been developed for the synthesis of new pyrano[3,2-c] and pyrano[3,2-a]carbazole de-rivatives via a three component reaction of 4-hydroxycarbazole or 2-hydroxycarbazole, isocyanides, and dialkylacetylenedi-carboxylates. Noteworthy features of this protocol include mild reaction conditions, catalyst-free, high atom-economy and high yields.

Synthesis of the six isomeric thieno[c]-fused 1,5- and 1,6-naphthyridines

1991 ◽  
Vol 56 (11) ◽  
pp. 2340-2351 ◽  
Author(s):  
Salo Gronowitz ◽  
Johan Malm ◽  
Anna-Britta Hörnfeldt
Keyword(s):  
Nmr Spectra ◽  
Coupling Reaction ◽  
One Pot ◽  
C Nmr

trough the use of Pd(0)-catalyzed coupling between 2- and 4-formyl-3-thiopheneboronic acids and 3-amino-2-bromopyridine and 4-acetamido-3-bromopyridine, convenient one-pot procedures for the preparation of thieno[2,3-c]-1,5-naphthyridine, thieno[3,4-c]-1,5-naphthyridine, thieno-[2,3-c]-1,6-naphthyridine, and thieno[3,4-c]-1,6-naphthyridine have been developed. In order to obtain thieno[3,2-c]-1,6-naphthyridine 2-(tributylstannyl)-3-thiophene aldehyde had to be used, since the organometallic partner in the coupling reaction, 3-formyl-2-thipheneboronic acid, is too easily deboronated. The effect of silver(I) oxide and thallium(I) carbonate on the coupling was studied. 1H and 13C NMR spectra of the six isomeric thieno{c]-fused 1,5- and 1,6-naphthyridines are discussed.

scholarly journals Fluorinated Iron(ii) clathrochelate units in metalorganic based copolymers: improved porosity, iodine uptake, and dye adsorption properties

RSC Advances ◽  
2021 ◽  
Vol 11 (25) ◽  
pp. 14986-14995
Author(s):  
Suchetha Shetty ◽  
Noorullah Baig ◽  
Atikur Hassan ◽  
Saleh Al-Mousawi ◽  
Neeladri Das ◽  
...  
Keyword(s):  
Dye Adsorption ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Building Blocks ◽  
Adsorption Properties ◽  
Iodine Uptake ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed

We report the synthesis of metalorganic copolymers made from the palladium catalyzed Sonogashira cross-coupling reaction between various iron(ii) clathrochelate building blocks with diethynyl–triptycene and fluorene derivatives.

Sign in / Sign up

Export Citation Format

Share Document