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3-Substituted tetrahydropyridopyrimidinone derivatives, method for producing the same, and their use

3-substituted tetrahydropyridopyrimidinone derivatives of the formula (I) wherein the radicals have the meanings given in the Description, to a method for producing said derivatives and, to their use for producing active ingredients for drugs.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Palladium-Catalyzed 2,2,2-Trifluoroethoxylation of Aromatic and Heteroaromatic Chlorides Utilizing Borate Salt and the Synthesis of a Trifluoro Analogue of Sildenafil

A simple and convenient method was developed for the introduction of a 2,2,2-trifluoroethoxy group to various aromatic and heteroaromatic systems. The novel process utilizes aromatic chlorides as substrates, and tetrakis(2,2,2-trifluoroethoxy) borate salt as an inexpensive and readily available fluoroalkoxy source in a palladium-catalyzed cross-coupling reaction. The power of the developed methodology was demonstrated in the synthesis of a fluorous derivative of Sildenafil.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 52409-22-0, name is Pd2(DBA)3, introducing its new discovery. Formula: C51H42O3Pd2

Benzimidazolyl Palladium Complexes as Highly Active and General Bifunctional Catalysts in Sustainable Cross-Coupling Reactions

A family of air- A nd moisture-stable dinuclear palladium complexes bearing 2-benzimidazolyl ligands is reported and shown to be a highly effective and general catalytic platform in diverse cross-coupling reactions. The rigidity and conformation of the ligand scaffold was readily modified via tethering of the 2-benzimidazolyl moiety to diamine ligands, resulting in significant changes in catalytic activity. Under optimal conditions, Suzuki, Heck, and Sonogashira-type couplings of aryl bromides can all be performed efficiently with good functional group compatibility using only 0.1 mola?% of catalyst, in aqueous or alcohol solvents. Experimental evidence highlights the importance of the bifunctional character of the ligand for catalytic activity, where the basic N-functionality in the ligand framework is proposed to accelerate (trans)metalation steps via intramolecular assistance.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Derivatives of DANPY (Dialkylaminonaphthylpyridinium), a DNA-Binding Fluorophore: Practical Synthesis of Tricyclic 2-Amino-6-bromonaphthalenes by Bucherer Reaction

A simple and convergent way to synthesize 2-amino-6-bromonaphthalenes involves condensation of free secondary amines with the corresponding 2-naphthol under Bucherer conditions. The amination protocol relies on common Teflon-capped pressure flasks and has been used to modify the tertiary aminonaphthalene core of DANPY, a biocompatible chromophore shown to be safe and effective for staining a variety of cellular targets. Following a Suzuki reaction with pyridine 4-boronic acid, additional diversity is introduced upon N-alkylation to install the pyridinium cation. New DANPY derivatives and intermediates reported herein reflect the modularity of the dye nucleus, including the addition of groups useful for applications in membrane staining and DNA-based biophotonics.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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INDANYLOXYPHENYLCYCLOPROPANECARBOXYLIC ACIDS

The present invention relates to compounds of general formula I, wherein the groups R1, R2, R3, m and n are defined as in claim 1, which have valuable pharmacological properties, in particular bind to the GPR40 receptor and modulate its activity. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2. Furthermore, the invention relates to novel intermediates, useful for the synthesis of compounds of formula I.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Highly Stereospecific Cross-Coupling Reactions of Anomeric Stannanes for the Synthesis of C-Aryl Glycosides

We demonstrate that configurationally stable anomeric stannanes undergo a stereospecific cross-coupling reaction with aromatic halides in the presence of a palladium catalyst with exceptionally high levels of stereocontrol. In addition to a broad substrate scope (>40 examples), this reaction eliminates critical problems inherent to nucleophilic displacement methods and is applicable to (hetero)aromatics, peptides, pharmaceuticals, common monosaccharides, and saccharides containing free hydroxyl groups.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Activator-free palladium-catalyzed silylation of aryl chlorides with silylsilatranes

The palladium-catalyzed silylation of aryl chlorides with silylsilatranes proceeds under activator-free conditions; hence, wide functional group compatibility is displayed and boryl and siloxy groups are able to survive. Experimental and computational studies revealed that smooth transmetalation from the silylsilatrane to the arylpalladium chloride is facilitated by strong interaction between the Lewis acidic silicon and the chloride.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Palladium-catalyzed cross-coupling of benzyl chlorides with cyclopropanol-derived ketone homoenolates

The palladium-catalyzed cross-coupling reaction of cyclopropanol-derived ketone homoenolates with benzyl chlorides is reported. This reaction proceeds in high yields with electron-neutral and electron-rich benzyl chlorides; however, yields are low with electron-poor benzyl chlorides. In addition, a range of cyclopropanols can be coupled in good yields. The reaction can be conducted with a low catalyst loading (1% Pd) and on a gram scale without reduction in yield.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Homo-and heterobimetallic Pd-, Ag-, and Ni-hybrid salen-bis-NHC complexes

salen ligands and N-heterocyclic carbenes (NHC) are among the most abundant structural ligand motifs for metal catalysis. In this article we present a modular approach to chiral ligands merging both ligand motifs for the preparation of bimetallic catalysts, in which one metal (M1) is coordinated by the salen moiety and the other metal (M2) binds to two NHCs. After selective complexation of M1 = PdII, Ni II ion into the salen N2O2 coordination site, heterobimetallic M1/Ag(I) complexes were synthesized which could be further utilized for the preparation of homo-and heterobimetallic M 1/PdII complexes by an oxidative transmetalation to Pd(0) as a key step of the catalyst synthesis. The structures of the bimetallic complexes and the intermetallic distances strongly depend on the counterions of M2 = PdII, as revealed by X-ray and UV-vis studies. In the absence of an anionic ligand with suitable Lewis basicity the salen oxygen atoms serve as bridging ligands for both metals. A preliminary investigation into catalysis showed that the complexes are capable of catalyzing the 1,4-addition of oxindoles to 2-nitrostyrene.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Palladium-Catalyzed Enantioselective Csp3-Csp3 Cross-Coupling for the Synthesis of (Poly)fluorinated Chiral Building Blocks

A general method for the enantioselective synthesis of carbo- and heterocyclic carbonyl compounds bearing fluorinated alpha-tetrasubstituted stereocenters using palladium-catalyzed decarboxylative allylic alkylation is described. The stereoselective Csp3-Csp3 cross-coupling reaction delivers five- and six-membered ketone and lactam products bearing (poly)fluorinated tetrasubstituted chiral centers in high yields and enantioselectivities. These fluorinated, stereochemically rich building blocks hold potential value in medicinal chemistry and are prepared using an orthogonal and enantioselective approach into such chiral moieties compared to traditional approaches, often without the use of electrophilic fluorinating reagents.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method