scholarly journals Hydroalkynylative cyclization of 1,6-enynes with terminal alkynes

2019 ◽  
Vol 10 (28) ◽  
pp. 6863-6867 ◽  
Author(s):  
Qi Teng ◽  
Nuligonda Thirupathi ◽  
Chen-Ho Tung ◽  
Zhenghu Xu
Keyword(s):  
Symmetry Breaking ◽  
Michael Addition ◽  
Terminal Alkynes ◽  
Reaction Proceeds

A rhodium-catalyzed highly regio- and enantioselective hydroalkynylation generating cis-hydrobenzofuranone-tethered enynes has been developed. The reaction proceeds with a dynamic kinetic head-to-head insertion and symmetry breaking Michael addition cascade.

Tandem Alkylation/Michael Addition Reaction of Dithiocarbamic Acids with Alkyl γ-Bromocrotonates: Access to Functionalized 1,3-Thiazolidine-2-thiones

Synthesis ◽  
2021 ◽  
Author(s):  
Azim Ziyaei Halimehjani ◽  
Petr Beier ◽  
Maryam Khalili Foumeshi ◽  
Ali Alaei ◽  
Blanka Klepetářová
Keyword(s):  
Amino Acids ◽  
Carbon Disulfide ◽  
Multicomponent Reaction ◽  
Michael Addition ◽  
Addition Reaction ◽  
Primary Amines ◽  
Oxidation Reactions ◽  
Michael Addition Reaction ◽  
Synthetic Utility ◽  
Reaction Proceeds

AbstractThiazolidine-2-thiones were prepared via a novel multicomponent reaction of primary amines (amino acids), carbon disulfide, and γ-bromocrotonates. The reaction proceeds via a domino alkylation/intramolecular Michael addition to provide the corresponding thiazolidine-2-thiones in high to excellent yields. By using diamines in this protocol, bis(thiazolidine-2-thiones) derivatives were synthesized. The synthetic utility of the adducts was demonstrated by hydrolysis, amidation, and oxidation reactions.

Synthesis of novel 1,2,3-triazole-substituted tomentosins

2019 ◽  
Vol 74 (3) ◽  
pp. 273-281 ◽  
Author(s):  
Mohamed Zaki ◽  
Abdelouahd Oukhrib ◽  
Ahmed El Hakmaoui ◽  
Marie-Aude Hiebel ◽  
Sabine Berteina-Raboin ◽  
...  
Keyword(s):  
Sesquiterpene Lactone ◽  
Column Chromatography ◽  
Michael Addition ◽  
Dipolar Cycloaddition ◽  
Terminal Alkynes

AbstractA series of 1,2,3-triazole-containing tomentosin scaffolds was obtained from tomentosin 1. The synthesis involved a Michael addition of trimethylsilylazide on the α-methylene-γ-lactone function of the natural sesquiterpene lactone 1 to give the diastereoisomers 2 and 3, which were readily separated by column chromatography. These compounds underwent copper-catalyzed Huisgen 1,3-dipolar cycloaddition with various terminal alkynes to provide compounds 4a–h and 5a–h in good yields.

Diversity-Oriented Synthesis via Catalyst-Free Addition of Ketones to [e]-Fused 1H-Pyrrole-2,3-diones

Synthesis ◽  
2018 ◽  
Vol 50 (24) ◽  
pp. 4897-4904 ◽  
Author(s):  
Ekaterina Stepanova ◽  
Andrey Maslivets ◽  
Svetlana Kasatkina ◽  
Maksim Dmitriev
Keyword(s):  
Intramolecular Cyclization ◽  
Aromatic Hydrocarbons ◽  
Michael Addition ◽  
Aldol Reaction ◽  
Synthetic Approach ◽  
Reaction Conditions ◽  
Diversity Oriented Synthesis ◽  
Catalyst Free ◽  
Solvent Free Conditions ◽  
Reaction Proceeds

A facile synthetic approach towards two distinct pyrrole-based heterocyclic scaffolds has been developed by the interaction of 1H-pyrrole-2,3-diones fused at the [e]-side to a 1,4-benzoxazin-2-one or quinoxalin-2(1H)-one moiety with ketones. The described interaction proceeds either as an aldol reaction or as a Michael addition/intramolecular cyclization depending on the reaction conditions. The disclosed aldol reaction proceeds with good diastereoselectivity under catalyst-free conditions when the reaction is carried out in aromatic hydrocarbons. Products of the cascade Michael addition/intramolecular cyclization reaction are predominantly formed under catalyst-free and solvent-free conditions. The proposed strategy provides facile access to pharmaceutically interesting pyrrole-based polyheterocycles.

The ruthenium-catalysed selective synthesis of mono-deuterated terminal alkynes

2016 ◽  
Vol 52 (24) ◽  
pp. 4509-4512 ◽  
Author(s):  
Basujit Chatterjee ◽  
Chidambaram Gunanathan
Keyword(s):  
Catalytic System ◽  
Deuterium Oxide ◽  
Selective Synthesis ◽  
Terminal Alkynes ◽  
Selective Activation ◽  
Highly Efficient ◽  
Chemoselective Synthesis ◽  
Reaction Proceeds

A highly efficient catalytic system is reported for chemoselective synthesis of mono-deuterated terminal alkynes using deuterium oxide in which the reaction proceeds via Ru–acetylide intermediates formed by selective activation of the sp-CH bond.

scholarly journals Solvent- and catalyst-free aza-Michael addition of imidazoles and related heterocycles

2020 ◽  
Author(s):  
Katharina Kodolitsch ◽  
Florian Gobec ◽  
Christian Slugovc
Keyword(s):  
Michael Addition ◽  
Catalyst Free ◽  
Michael Acceptor ◽  
Reaction Proceeds ◽  
Azole Derivative ◽  
Small Excess

This work demonstrates the scope and limitations of the aza-Michael addition of imidazoles and related heterocycles with electron deficient olefins under solvent- and catalyst-free conditions. The reaction proceeds at 80°C within hours towards completion as long as the azole derivative is sufficiently soluble in the Michael acceptor, which has been used in small excess. Workup only comprises evaporation of surplus Michael-acceptor and no additional solvents are necessary for purifying the products.<br>

scholarly journals Dearomative Michael addition involving enals and 2-nitrobenzofurans realized under NHC-catalysis

2022 ◽  
Author(s):  
Mateusz Dyguda ◽  
Anna Skrzyńska ◽  
Lesław Sieroń ◽  
Łukasz Albrecht
Keyword(s):  
Michael Addition ◽  
Unsaturated Aldehydes ◽  
Reaction Proceeds ◽  
Michael Acceptors ◽  
High Yields

In the manuscript the first enantioselective dearomative Michael addition between α,β-unsaturated aldehydes and 2-nitrobenzofurans realized under N-heterocyclic carbene activation has been described. The reaction proceeds via addition of homoenolate to Michael acceptors leading to the formation of biologically important heterocycles with high yields and stereoselectivities. Their functionalization potential has been confirmed in selected, diastereoselective transformations.

scholarly journals Enantioselective Synthesis of Chromanones Bearing an α,α-Disubstituted α-Amino Acid Moiety via Decarboxylative Michael Reaction

Molecules ◽  
2019 ◽  
Vol 24 (14) ◽  
pp. 2565 ◽  
Author(s):  
Jan Bojanowski ◽  
Lesław Sieroń ◽  
Anna Albrecht
Keyword(s):  
Amino Acid ◽  
Acid Derivative ◽  
Michael Addition ◽  
Structural Unit ◽  
Michael Reaction ◽  
Enantioselective Synthesis ◽  
Amino Acid Derivative ◽  
Acid Moiety ◽  
Amino Acid Moiety ◽  
Reaction Proceeds

In this manuscript, a novel, decarboxylative Michael reaction between α-substituted azlactones and chromone-3-carboxylic acids is described. The reaction proceeds in a sequence Michael addition followed by decarboxylative deprotonation, and it results in the formation of chromanones bearing an azlactone structural unit. The possibility of transforming an azlactone moiety into a protected α,α-disubstituted α-amino acid derivative is also demonstrated.

Green H2O-Promoted Solvent-Free Synthesis of Enaminocarbonyl Compounds with High Stereoselectivity from Electron-Deficient Terminal Alkynes

Synlett ◽  
2020 ◽  
Vol 31 (09) ◽  
pp. 878-882
Author(s):  
Xiao Yun Chen ◽  
Luming Zhang ◽  
Yaonan Tang ◽  
Shuxia Yuan ◽  
Baocheng Zhu ◽  
...  
Keyword(s):  
Michael Addition ◽  
Aromatic Amines ◽  
Solvent Free ◽  
Secondary Amines ◽  
Terminal Alkynes ◽  
Primary Aromatic Amines ◽  
Solvent Free Synthesis ◽  
High Stereoselectivity

A green H2O-promoted solvent-free hydroamination of electron-deficient terminal alkynes with amines has been developed. All secondary amines, including aliphatic and aromatic amines, gave the corresponding (E)-enamines in good to excellent yields, whereas primary aromatic amines afforded Z-configured products in moderate yields. Propiolates, propyn-1-ones, propynamides, and 1-(ethynylsulfonyl)-4-methylbenzene were explored in this Michael addition.

Base-Promoted Tandem Cyclization for the Synthesis of Polyfunctional 2-Hydroxy-2,3-dihydrofurans from Arylglyoxal Monohydrates and 3-(1H-Indol-3-yl)-3-oxopropanenitrile

Synlett ◽  
2018 ◽  
Vol 29 (14) ◽  
pp. 1926-1932
Author(s):  
Yi Liu ◽  
An-Xin Wu ◽  
Qun Cai ◽  
Hui-Yang Sheng ◽  
Deng-Kui Li
Keyword(s):  
Functional Groups ◽  
Michael Addition ◽  
Knoevenagel Condensation ◽  
One Pot ◽  
Wide Range ◽  
Reaction Proceeds ◽  
Tandem Cyclization ◽  
Arylglyoxal Monohydrates

An efficient base-promoted tandem cyclization for the synthesis of polyfunctional 2-hydroxy-2,3-dihydrofurans from arylglyoxal monohydrates and 3-(1H-indol-3-yl)-3-oxopropanenitrile has been established. The investigation of the mechanism suggested that this reaction proceeds through a Knoevenagel condensation–Michael addition–oxidation–cyclization sequence. This method demonstrates the compatibility with a wide range of functional groups to produce the 2-hydroxy-2,3-dihydrofuran scaffolds in good to excellent yields in one pot.

scholarly journals Solvent- and catalyst-free aza-Michael addition of imidazoles and related heterocycles

2020 ◽  
Author(s):  
Katharina Kodolitsch ◽  
Florian Gobec ◽  
Christian Slugovc
Keyword(s):  
Michael Addition ◽  
Catalyst Free ◽  
Michael Acceptor ◽  
Reaction Proceeds ◽  
Azole Derivative ◽  
Small Excess

This work demonstrates the scope and limitations of the aza-Michael addition of imidazoles and related heterocycles with electron deficient olefins under solvent- and catalyst-free conditions. The reaction proceeds at 80°C within hours towards completion as long as the azole derivative is sufficiently soluble in the Michael acceptor, which has been used in small excess. Workup only comprises evaporation of surplus Michael-acceptor and no additional solvents are necessary for purifying the products.<br>

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