scholarly journals Thiol-free chemoenzymatic synthesis of β-ketosulfides

2019 ◽  
Vol 15 ◽  
pp. 378-387
Author(s):  
Adrián A Heredia ◽  
Martín G López-Vidal ◽  
Marcela Kurina-Sanz ◽  
Fabricio R Bisogno ◽  
Alicia B Peñéñory
Keyword(s):  
Multicomponent Reaction ◽  
Chemical Diversity ◽  
Chemoenzymatic Synthesis ◽  
Selective Synthesis ◽  
High Chemical ◽  
One Pot ◽  
Mild Conditions ◽  
Set Up ◽  
Sulfur Donor

A preparation of β-ketosulfides avoiding the use of thiols is described. The combination of a multicomponent reaction and a lipase-catalysed hydrolysis has been developed in order to obtain high chemical diversity employing a single sulfur donor. This methodology for the selective synthesis of a set of β-ketosulfides is performed under mild conditions and can be set up in one-pot two-step and on a gram-scale.

scholarly journals Application of One-Pot Three-Component Condensation Reaction for the Synthesis of New Organophosphorus–Sulfur Macrocycles

Synlett ◽  
2018 ◽  
Vol 29 (11) ◽  
pp. 1496-1501 ◽  
Author(s):  
J. Woollins ◽  
Guoxiong Hua ◽  
David Cordes ◽  
Alexandra Slawin
Keyword(s):  
Multicomponent Reaction ◽  
Room Temperature ◽  
Condensation Reaction ◽  
Synthesis Method ◽  
Membered Ring ◽  
One Pot ◽  
X Ray ◽  
Efficient Approach ◽  
Mild Conditions ◽  
Sulfur Heterocycles

An efficient approach has been developed for the synthesis of new phosphorus–sulfur heterocycles by a one-pot three-component condensation reaction of a four-membered-ring thionation reagent [Lawesson’s reagent or its ferrocene analogue (2,4-diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide)], an alkane- or arenedithiol, and a dihaloalkane at room temperature in the presence of triethylamine. The simple synthesis method with mild conditions (room temperature and normal reactant concentrations) enhances further the application of the multicomponent reaction in the preparation of novel phosphorus–sulfur heterocycles. Six representative X-ray structures confirmed the formation of these macrocycles.

Efficient Synthesis of 5-Trifluoromethylthio-1,2,3-Triazoles: One-Pot Multicomponent Reaction from Elemental Sulfur and TMSCF3

Synthesis ◽  
2019 ◽  
Vol 52 (02) ◽  
pp. 304-310 ◽  
Author(s):  
Lin-Lin Zhang ◽  
Meng-Tian Li ◽  
Liang-Liang Shen ◽  
Qin-Pei Wu
Keyword(s):  
Multicomponent Reaction ◽  
Elemental Sulfur ◽  
Efficient Synthesis ◽  
One Pot ◽  
Mild Conditions ◽  
Multistep Reaction ◽  
Easy Operation

A sequential multistep reaction toward 5-trifluoromethyl­thio-1,2,3-triazoles has been established, starting from alkynes, organo­azides, S8, and (trifluoromethyl)trimethylsilane (TMSCF3). This reaction features mild conditions, easy operation, and readily available substrates.

scholarly journals An Artificial Intelligence that Discovers Unpredictable Chemical Reactions

2020 ◽  
Author(s):  
Dario Caramelli ◽  
Jaroslaw Granda ◽  
Dario Cambié ◽  
Hessam Mehr ◽  
Alon Henson ◽  
...  
Keyword(s):  
Neural Network ◽  
Artificial Intelligence ◽  
Deep Learning ◽  
Convolutional Neural Network ◽  
Chemical Reactions ◽  
Multicomponent Reaction ◽  
Cascade Reaction ◽  
One Pot ◽  
Single Substrate ◽  
Set Up

<p><b>We present an artificial intelligence, built to autonomously explore chemical reactions in the laboratory using deep learning. The reactions are performed automatically, analysed online, and the data is processed using a convolutional neural network (CNN) trained on a small reaction dataset to assess the reactivity of reaction mixtures. The network can be used to predict the reactivity of an unknown dataset, meaning that the system is able to abstract the reactivity assignment regardless the identity of the starting materials. The system was set up with 15 inputs that were combined in 1018 reactions, the analysis of which lead to the discovery of a ‘multi-step, single-substrate’ cascade reaction and a new mode of reactivity for methylene isocyanides. <i>p</i>-Toluenesulfonylmethyl isocyanide (TosMIC) in presence of an activator reacts consuming six equivalents of itself to yield a trimeric product in high (unoptimized) yield (47%) with formation of five new C-C bonds involving <i>sp</i>-<i>sp<sup>2</sup></i> and <i>sp</i>-<i>sp<sup>3</sup></i> carbon centres. A cheminformatics analysis reveals that this transformation is both highly unpredictable and able to generate an increase in complexity like a one-pot multicomponent reaction.</b></p>

scholarly journals An Artificial Intelligence that Discovers Unpredictable Chemical Reactions

2020 ◽  
Author(s):  
Dario Caramelli ◽  
Jaroslaw Granda ◽  
Dario Cambié ◽  
Hessam Mehr ◽  
Alon Henson ◽  
...  
Keyword(s):  
Neural Network ◽  
Artificial Intelligence ◽  
Deep Learning ◽  
Convolutional Neural Network ◽  
Chemical Reactions ◽  
Multicomponent Reaction ◽  
Cascade Reaction ◽  
One Pot ◽  
Single Substrate ◽  
Set Up

<p><b>We present an artificial intelligence, built to autonomously explore chemical reactions in the laboratory using deep learning. The reactions are performed automatically, analysed online, and the data is processed using a convolutional neural network (CNN) trained on a small reaction dataset to assess the reactivity of reaction mixtures. The network can be used to predict the reactivity of an unknown dataset, meaning that the system is able to abstract the reactivity assignment regardless the identity of the starting materials. The system was set up with 15 inputs that were combined in 1018 reactions, the analysis of which lead to the discovery of a ‘multi-step, single-substrate’ cascade reaction and a new mode of reactivity for methylene isocyanides. <i>p</i>-Toluenesulfonylmethyl isocyanide (TosMIC) in presence of an activator reacts consuming six equivalents of itself to yield a trimeric product in high (unoptimized) yield (47%) with formation of five new C-C bonds involving <i>sp</i>-<i>sp<sup>2</sup></i> and <i>sp</i>-<i>sp<sup>3</sup></i> carbon centres. A cheminformatics analysis reveals that this transformation is both highly unpredictable and able to generate an increase in complexity like a one-pot multicomponent reaction.</b></p>

One-Pot Synthesis of Polysubstituted Imidazoles Based on Pd(OAc)2/Ce(SO4)2/Bi(NO3)3 Trimetallic Cascade of Decarboxylation/Wacker-Type Oxidation/Debus–Radziszewski Reaction

Synthesis ◽  
2019 ◽  
Vol 51 (17) ◽  
pp. 3221-3230 ◽  
Author(s):  
Wei Sun ◽  
Mingjuan Zhang ◽  
Peilang Li ◽  
Yiqun Li
Keyword(s):  
Catalytic System ◽  
Multicomponent Reaction ◽  
Functional Group ◽  
Cascade Process ◽  
One Pot ◽  
Aryl Aldehydes ◽  
Mild Conditions ◽  
One Pot Synthesis ◽  
System A

A novel and highly efficient one-pot synthesis of polysubstituted imidazoles from α-hydroxyphenylacetic acids, diphenylacetylene, and amines has been achieved by Pd(OAc)2/Ce(SO4)2/Bi(NO3)3 trimetallic catalytic system. A series of control experiments showed that this overall reaction occurs through a one-pot cascade process combining the steps of decarboxylation of α-hydroxyphenylacetic acids, Wacker-type oxidation of diphenylacetylene, and Debus–Radziszewski annulation of aryl aldehydes and benzil generated in situ, as well as amines. This reaction represents a novel multicomponent reaction using α-hydroxyphenylacetic acids and diphenylacetylene as sources of aryl aldehydes and a β-diketone. This process exhibits a broad substrate scope and a good functional group tolerance to assemble the corresponding polysubstituted imidazoles in excellent yields (72–88%) under mild conditions.

scholarly journals Microwave-Assisted, One-Pot Synthesis of Doxycycline under Heterogeneous Catalysis in Water

Antibiotics ◽  
2021 ◽  
Vol 10 (9) ◽  
pp. 1084
Author(s):  
Fabio Bucciol ◽  
Elia Maffeis ◽  
Emanuela Calcio Gaudino ◽  
László Jicsinszky ◽  
Silvia Tagliapietra ◽  
...  
Keyword(s):  
Heterogeneous Catalysis ◽  
Microwave Irradiation ◽  
Rhodium Catalyst ◽  
Selective Synthesis ◽  
Cyclodextrin Complex ◽  
One Pot ◽  
Mild Conditions ◽  
Microwave Assisted ◽  
One Step ◽  
Pharmaceutical Molecules

The selective synthesis of active pharmaceutical molecules is a challenging issue, particularly when attempting to make the reactions even more sustainable. The present work focuses on the microwave-assisted hydrogenolysis of oxytetracycline to selectively produce α-doxycycline. Although the combination of microwave irradiation and a heterogeneous rhodium catalyst provided good conversions, the selective synthesis of active α-doxycycline was only achieved when an oxytetracycline-cyclodextrin complex was used as the starting material, giving the desired product at 34.0% yield in a one-step reaction under very mild conditions.

A One-Pot Chemoenzymatic Synthesis of (2S,4R)-4-Methylproline Enables the First Total Synthesis of Antiviral Lipopeptide Cavinafungin B

2018 ◽  
Author(s):  
Christian R. Zwick ◽  
Hans Renata
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Complex Molecule ◽  
Molecular Target ◽  
Chemoenzymatic Synthesis ◽  
General Strategy ◽  
One Pot

We report an efficient ten-step synthesis of antiviral natural product cavinafungin B in 37% overall yield. By leveraging a one-pot chemoenzymatic synthesis of (2S,4R)-4-methylproline and oxazolidine-tethered (Rink-Boc-ATG-resin) SPPS methodology, the assembly of our molecular target could be conducted in an efficient manner.This general strategy could prove amenable to the construction of other natural and unnatural linear lipopeptides. The value of incorporating biocatalytic steps in complex molecule synthesis is highlighted by this work.

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