31330-51-5

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 26, p. 2738, 1961 DOI: 10.1021/jo01066a029

InChI:InChI=1/C10H9NO2S/c1-2-13-10(12)8(7-11)6-9-4-3-5-14-9/h3-6H,2H2,1H3/b8-6+

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 105-56-6 ethyl 2-cyanoacetate 
• 5370-67-2 2-(dimethoxymethyl)thiophene 
• 636-72-6 2-thiophenemethanol 

Downstream Products

• 87736-69-4 4-thenylidene-1-phenyl-2-thioxoimidazolidin-5-one 
• 87736-61-6 ethyl 2-amino-5-cyano-6-phenyl-4-(2-thienyl)-4H-pyran-3-carboxylate 
• 126440-96-8 5-Methyl-2-phenyl-4-[1-thiophen-2-yl-meth-(E)-ylidene]-2,4-dihydro-pyrazol-3-one 
• 112906-28-2 2-amino-4,6-di(thiophen-2-yl)isophthalonitrile 

Relevant academic research and scientific papers

Highly Active Copper(I)-Chalcogenone Catalyzed Knoevenagel Condensation Reaction Using Various Aldehydes and Active Methylene Compounds

First copper(I) chalcogenones catalysed Knoevenagel Condensation reactions have been reported. No illustration of the utilization of this copper-chalcogenone complex class in Knoevenagel Condensation catalysis can be found. Thus, copper(I) bis(benzimidazole-2-chalcogenone) catalysts [Cu(L1)4]+BF4? (1) and [Cu(L2)4]+BF4? (2) (L1 = bis(1-isopropyl-benzimidazole-2-selone)-3-ethyl; L2 = bis(1-isopropyl-benzimidazole-2-thione)-3-ethyl) have been utilized as catalysts in the Knoevenagel Condensation reactions. These copper(I) chalcogenone catalysts have shown high efficiency for the catalytic Knoevenagel Condensation of aryl aldehydes and active methylene compounds. In particular, complex 2, exhibit the best catalytic activities. The scope of the catalytic reactions has been investigated with 22 different molecules. The excellent catalytic activity has been depicted for various types of substrates with either electron-rich or deficient aryl aldehydes. The present investigation features relatively mild reaction conditions with good functional group tolerance and excellent yields. Graphic Abstract: The first copper(I)-chalcogenone complexes catalysed Knoevenagel Condensation reactions?have also been investigated, and revealed the best catalytic activities. [Figure not available: see fulltext.]

INHIBITORS OF α-AMINO-β-CARBOXYMUCONIC ACID SEMIALDEHYDE DECARBOXYLASE

The present disclosure discloses compounds capable of modulating the activity of α-amino-β-carboxymuconic acid semialdehyde decarboxylase (ACMSD), which are useful for the prevention and/or the treatment of diseases and disorders associated with defects in NAD+ biosynthesis, e.g., metabolic disorders, neurodegenerative diseases, chronic inflammatory diseases, kidney diseases, and diseases associated with ageing. The present application also discloses pharmaceutical compositions comprising said compounds and the use of such compounds as a medicament.

Novel synthesis of 3-cyano-2-pyridones derivatives catalyzed by Au–Co/TiO2

Abstract: The current work described a new and highly selective method for the synthesis of substituted 3-cyano-2-pyridones scaffolds using gold-cobalt supported on TiO2 as a robust and recyclable catalyst. The products were successfully obtained by one-pot, multicomponent manner. This procedure generated the desired products 2-pyridones derivatives in good yields, from simple and available starting materials using heterogeneous and reusable catalyst. The diversity of 3-cyano-2-pyridones derivatives was prepared and characterized by IR, 1H and 13C NMR data and confirmed by element analysis data. Graphic abstract: [Figure not available: see fulltext.].

Amino Acid Amide based Ionic Liquid as an Efficient Organo-Catalyst for Solvent-free Knoevenagel Condensation at Room Temperature

Abstract: Ionic liquids of amino acid amide were synthesized and used as an efficient catalyst for solvent-free Knoevenagel condensation. Synthesized ionic liquids are an environmentally benign, inexpensive, metal free and plays the dual role of solvent as well as an efficient catalyst for Knoevenagel condensation. A wide range of aliphatic, aromatic and heteroaromatic aldehydes easily undergo condensation with malononitrile and ethyl cyanoacetate. The reaction proceeds at room temperature without using any organic solvent and is very fast with good to excellent yield. Additionally, the catalyst is easily separable and recyclable without loss of activity. Graphic Abstract: [Figure not available: see fulltext.].

Prolinamide functionalized polyacrylonitrile fiber with tunable linker length and surface microenvironment as efficient catalyst for Knoevenagel condensation and related multicomponent tandem reactions

A series of new prolinamide polyacrylonitrile fiber catalysts with tunable length of alkyl linker and different linker group were prepared by covalent bonding for the first time and well characterized by mechanical strength, FT-IR, XRD, EA, TGA, SEM and water contact angel. The catalytic activities of these fiber catalysts were evaluated in Knoevenagel condensation and one-pot Knoevenagel-Michael multicomponent tandem reactions to synthesize α, β-unsaturated nitrile and 2-amino-4H-chromene derivatives in water. The result show that the suitable linker length attaching amines to fiber matrix as well as the constructed hydrophobic microenvironment by linker group within the surface layers of fiber materials effectively promotes the reactions. In addition, the good swollen capacity of fiber in solvent ensure that the reaction proceed well. Fiber catalyst PANPA?2F modified by prolinamide with a C2 alkyl chain exhibited the best catalytic performance and can be easily recovered and reused for at least ten consecutive cycles without significant loss of catalytic activity and active sites leaching.

Polymer immobilized [Mg@PS-anthra] complex: An efficient recyclable heterogeneous catalyst for the incorporation of carbon dioxide into oxiranes at atmospheric pressure and Knoevenagel condensation reaction under solvent free condition

Chemical fixation of CO2 into the organic molecules is very challenging from the perspective of greenhouse gas consumption and manufacturing of chemicals with C1 backbone. The process was developed with the synthesis of an efficient polystyrene

Synthesis of multifunctional polymer containing Ni-Pd NPs via thiol-ene reaction for one-pot cascade reactions

Recently, acid–base bifunctional catalysts have been considered due to their abilities, such as the simultaneous activation of electrophilic and nucleophilic species and their high importance in organic syntheses. However, the synthesis of acid–base catalysts is problematic due to the neutralization of acidic and basic groups. This work reports a facial approach to solve this problem via the synthesis of a novel bifunctional polymer using inexpensive materials and easy methods. In this way, at the first step, heterogeneous poly (styrene sulfonic acid-n-vinylimidazole) containing pentaerythritol tetra-(3-mercaptopropionate) (PETMP) and trimethylolpropane trimethacrylate (TMPTMA) cross-linkers were synthesized in the pores of a mesoporous silica structure using click reaction as a novel bifunctional acid–base catalyst. After that, Ni-Pd nanoparticles supported on poly (styrenesulfonic acid-n-vinylimidazole)/KIT-6 as a novel trifunctional heterogeneous acid–base-metal catalyst was prepared. The prepared catalysts were characterized by various techniques like FT-IR, TGA, ICP-AES, DRS-UV, TEM, FE-SEM, EDS-Mapping, and XRD. The synthesized catalysts were efficiently used as bifunctional/trifunctional catalysts for one-pot, deacetalization-Knoevenagel condensation and one-pot, three-step and a sequential reaction containing deacetalization-Knoevenagel condensation-reduction reaction. It is important to note that the synthesized catalyst showing high chemo-selectivity for the reduction of nitro group, alkenyl double bond and ester group in the presence of nitrile. Moreover, it was found that the different nanoparticles including Ni, Pd, and alloyed Ni-Pd showing different chemo-selectivity and catalytic activity in the reaction.

Layered double hydroxide anchored ionic liquids as amphiphilic heterogeneous catalysts for the Knoevenagel condensation reaction

In recent years, great attention has been dedicated to the development of heterogeneous base catalysts providing a green and sustainable process in benign aqueous media. Herein, the ionic liquid modified layered double hydroxide (LDH) based catalysts of L

l-Lysine Functionalized Polyacrylonitrile Fiber: A Green and Efficient Catalyst for Knoevenagel Condensation in Water

Abstract: The l-lysine functionalized polyacrylonitrile fiber (PANLF) was prepared by grafting the l-lysine into a commercially available polyacrylonitrile fiber and showed highly catalytic activity for Knoevenagel condensation reaction. With low temperature (45?°C) and short reaction time (1?h), the fiber catalyst was well applicable to Knoevenagel condensation of a wide range of aldehydes and the yields could reach up to 99%. Interestingly, only in water could the reaction take place smoothly (with a yield of 88%) and a polar micro-environment promoted reaction process had been proposed to explain this phenomenon. Besides, the fiber catalyst has advantages of easy preparation, high functional degree, strong mechanical strength and thermal stability, etc. And it can be reused at least 5 times without further treatment and performed well in scaled-up experiment (amplified 50 times) and flow chemistry experiment (no loss of catalytic activity after 48?h), which indicates its potential application in industry application. Graphical Abstract: [Figure not available: see fulltext.].

Asymmetric Reaction of p-Quinone Diimide: Organocatalyzed Michael Addition of α-Cyanoacetates

Hitherto unknown catalytic enantioselective transformation of p-quinone diimides is achieved using chiral bifunctional organic molecules. Bifunctional thiourea compounds catalyze the Michael addition of cyanoacetates with excellent yields and enantioselec