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TiO2 Nanoparticles Catalyzed Chemoselective Synthesis of 2-Chloroquinolinyl-4-quinolinones and their Intramolecular Cyclization through Palladium Catalyzed Sonogashira Coupling Reaction

Abstract: The 2-chloro-3-formyl quinolines 1, were chemoselectivity and effectively converted into their corresponding 2-chloroquinolinyl-4-quinolinones 3 through Knoevenagel condensation/aza-Michael addition utilizing TiO2 nanoparticles. The Sonogashira coupling of 2-chloroquinolinyl moiety of the quinolinone, 3 gave unprecedented cyclised products 1,6-naphthyridines, 5 through cascade reaction in good yields and purity. Graphical Abstract: [Figure not available: see fulltext.]

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

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Nonsymmetrical 3,4-dithienylmaleimides by cross-coupling reactions with indium organometallics: Synthesis and photochemical studies

The synthesis and photochemical study of novel nonsymmetrical 1,2-dithienylethenes (DTEs) with a maleimide bridge have been carried out. The synthetic approach to the DTEs was based on successive selective palladium-catalyzed cross-coupling reactions of 5-susbtituted-2-methyl-3-thiophenyl indium reagents with 3,4-dichloromaleimides. The required organoindium reagents were prepared from 2-methyl-3,5-dibromothiophene by a selective (C-5) coupling reaction with triorganoindium compounds (R3In) and subsequent metal-halogen exchange. The coupling reactions usually gave good yields and have a high atom economy with substoichiometric amounts of R3In. The results of photochemical studies show that these novel dithienylmaleimides undergo a photocyclization reaction upon irradiation in the UV region and a photocycloreversion after excitation in the visible region, thus they can be used as photochemical switches. ON-OFF operations can be repeated in successive cycles without appreciable loss of effectiveness in the process.

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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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Concise synthesis of prenylated and geranylated chalcone natural products by regiospecific iodination and Suzuki coupling reactions

Four natural chalcones bearing prenyl or geranyl groups, i.e., isobavachalcone (1), bavachalcone (2), xanthoangelol (3), and 2?,4?,4-trihydroxy-5?-geranylchalcone (isoxanthoangelol, 4) were synthesized by using a regio-selective iodination and the Suzuki coupling reaction as key steps. Among them, the first total synthesis of 2?,4?,4-trihydroxy-5?-geranylchalcone was achieved in 36% overall yield. Comparing with the reported methods based on C-alkylation or O-alkylation followed by Claisen rearrangement to introduce the side chain, this new strategy capitalizes on a precious regiochemical control during iodination. The overall yields for the synthesis of the first three chalcones were improved from 17% to 53%, 12% to 35%, and 28% to 50%, respectively.

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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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Kumada – Corriu coupling of Grignard reagents, probed with a chiral Grignard reagent

The Grignard reagent 2, in which the magnesium-bearing carbon atom is the sole stereogenic centre has been coupled with vinyl bromide under Pd(0) or Ni(0)-catalysis to give compound 3 with full retention of configuration. Coupling using Fe(acac)3 or Co(acac)2 as catalyst was accompanied by considerable racemisation. These findings are discussed with respect to a dichotomy between concerted polar and stepwise SET transmetallation pathways.

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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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(S)-4-(Difluoromethyl)-5-(4-(3-methylmorpholino)-6-morpholino-1,3,5-triazin-2-yl)pyridin-2-amine (PQR530), a Potent, Orally Bioavailable, and Brain-Penetrable Dual Inhibitor of Class i PI3K and mTOR Kinase

The phosphoinositide 3-kinase (PI3K)/mechanistic target of rapamycin (mTOR) pathway is frequently overactivated in cancer, and drives cell growth, proliferation, survival, and metastasis. Here, we report a structure-activity relationship study, which led to the discovery of a drug-like adenosine 5?-triphosphate-site PI3K/mTOR kinase inhibitor: (S)-4-(difluoromethyl)-5-(4-(3-methylmorpholino)-6-morpholino-1,3,5-triazin-2-yl)pyridin-2-amine (PQR530, compound 6), which qualifies as a clinical candidate due to its potency and specificity for PI3K and mTOR kinases, and its pharmacokinetic properties, including brain penetration. Compound 6 showed excellent selectivity over a wide panel of kinases and an excellent selectivity against unrelated receptor enzymes and ion channels. Moreover, compound 6 prevented cell growth in a cancer cell line panel. The preclinical in vivo characterization of compound 6 in an OVCAR-3 xenograft model demonstrated good oral bioavailability, excellent brain penetration, and efficacy. Initial toxicity studies in rats and dogs qualify 6 for further development as a therapeutic agent in oncology.

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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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A pseudo-rotaxane based on an iridium(III)-copper(I) dyad

The synthesis of a pseudo-rotaxane containing two metal centres has been achieved using the coordination of a ditopic organic ligand on an iridium(III) complex followed by the coordination of a copper(I) centre. Preliminary photophysical studies indicate that the excited state of the iridium is quenched by the copper unit.

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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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Synthesis, structural characterization, and unusual field-effect behavior of organic transistor semiconductor oligomers: Inferiority of oxadiazole compared with other electron-withdrawing subunits

A new series of heterocyclic oligomers based on the 1,3,4-oxadiazole ring were synthesized. Other electron-deficient cores (fluorenone and fumaronitrile) were introduced to investigate the oligomers as n-channel materials. The physical properties, thin film morphologies, and field-effecttransistor characteristics of the oligomers were evaluated. Thin films were deposited at different substrate temperatures and on variously coat ed Si/Si02 for device optimization. Contrary to our expectations, the thin film devices of 4 revealed p-channel behavior, and the average hole mobility was 0.14 cm 2 V-1 s-1 (maximum value 0.18 cm2 V-1 s-1). Compound 11 is the first example of an oxadiazole-containing organic semiconductor (OSC) oligomer in an n-channel organic field-effect transistor (OFET) and shows moderate mobilities. Non- oxadiazole-containing oligomers 9 and 12 showed n-channel OFET behavior on hexamethyldisilazane- treated and Cytop spin-coated Si02 in vacuum. These are the first fluorenone- and fumaronitrile-based n-OSCs demonstrated in transistors. However, oxadiazole-core materials 14 and 16 were inactive in transistordevices.

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

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Suzuki-Miyaura Diversification of Amino Acids and Dipeptides in Aqueous Media

The Suzuki-Miyaura derivatisation of free amino acids, peptides and proteins is an attractive area with considerable potential utility for medicinal chemistry and chemical biology. Here we report the modification of unprotected and Boc-protected aromatic amino acids and dipeptides in aqueous media, enabling heteroarylation and vinylation. We systematically investigate the impact of the peptide backbone and adjacent amino acid residues upon the reaction. Our studies reveal that although asparagine and histidine hinder the reaction, by utilising dppf, a ferrocene-based bidentate phosphine ligand, cross coupling of halophenylalanine or halotryptophan adjacent to such a residue could be enabled. Our studies reveal dppf to have good compatibility with all unprotected, proteinogenic amino acid side chains.

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

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Facile synthesis of beta-derivatized porphyrins – Structural characterization of a beta – beta-bis-porphyrin

A generally applicable Suzuki methodology for the synthesis of beta- derivatized porphyrins has been developed starting from bromoporphyrin 1, which is converted into an air- and water-stable boronate derivative. Metal- mediated cross-coupling of the latter compound with various aryl bromides furnishes beta-arylporphyrins 2 with yields similar to those reported for derivatization at the meso-position. The utility of the method was demonstrated with the preparation and structural characterization of bis- porphyrin 3, directly linked at the beta-positions of the rings.

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Palladium/carbon catalyst regeneration and mechanical application method

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A divergent synthesis of oligoarylalkanethiols with Lewis-basic N-donor termini

Araliphatic thiols are key molecules for the formation of self-assembled monolayers with high long-range order. If these monolayers shall act as bases for the attachment of other molecules, the respective thiols need to carry suitable functional groups, such as the amino or the pyridine group. Due to their Lewis-basicity, these groups are not compatible with the thiol group under most reaction conditions. Here, an entry into this versatile class of compounds is presented, by using fundamental building blocks in which the thiol groups are protected as triisopropylsilyl sulfides making them compatible with many reagents including Grignard reagents and palladium catalysts. With this strategy at hand, six thiols with bi- and terphenyl backbones, one to three methylene groups, and amino or pyridine head groups became accessible in short reaction sequences. The Royal Society of Chemistry 2010.

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