Solid-Phase Synthesis of <i>N</i>-Bi- and <i>N</i>-Terarylpiperazines via Three Different and Consecutive Palladium-Catalyzed Cross-Coupling Reactions

Ruhland, Thomas; Svejgaard, Lars; Rasmussen, Lars K.; Andersen, Kim

doi:10.1021/cc0499439

Cited by 8 publications

(5 citation statements)

References 23 publications

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“…Synthetic methodology was described for constructing libraries of alkaloid-like compounds 204a-e 390 and macrocycles 208. 334 Skeletal diversity in 204 was achieved by manipulating resin-bound reactive dihydroisoquinoline and dihydropyridine intermediates. Statistical and computational analyses were carried out to understand the relationship between structure and cell activity.…”

Section: Small Molecule Library For Gpcrs Activated Bymentioning

confidence: 99%

“…This is analogous to the process of protein folding in which primary amino acid sequences (“σ-elements”) are transformed into diverse 3-dimensional structures. Synthetic methodology was described for constructing libraries of alkaloid-like compounds 204a − e 390 and macrocycles 208 . Skeletal diversity in 204 was achieved by manipulating resin-bound reactive dihydroisoquinoline and dihydropyridine intermediates.…”

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confidence: 99%

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Comprehensive Survey of Combinatorial Library Synthesis: 2004

Dolle

2005

J. Comb. Chem.

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An exhaustive compilation of biologically active libraries covering the years 1992-1997 was presented in a previous review [1a]. In that review, libraries were divided among 4 major categories, including those active against proteases, non-proteolytic enzymes, Gprotein coupled receptors, and non-G-protein coupled receptors. A generic structure for each library was provided as well as the structure of the most active member. The number of biologically active libraries reported in the literature during this time period (86 total) represents <25% of the total number of published library constructs. Disclosure of library synthesis without accompanying screening data is a more common occurrence. Because these types of libraries are equally important to the practicing combinatorial chemist, it was thought that a comprehensive listing of such libraries spanning the years 1992-1997 would be a useful supplement to the previous review [1a,b].Library constructs [2-248] listed herein are relegated to one of five tables. Table 1 is entitled 'Scaffold derivatization' and includes all constructs in which a multi-functional scaffold is modified in some fashion to create a library. An example of a construct found in Table 1 would be the sequential addition of three nucleophiles to trichloropyrimidine. Table 2, entitled 'Acyclic synthesis', lists all linear constructs such as those derived from multi-component Ugi condensations.

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Section: Small Molecule Library For Gpcrs Activated Bymentioning

confidence: 99%

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confidence: 99%

Comprehensive Survey of Combinatorial Library Synthesis: 2004

Dolle

2005

J. Comb. Chem.

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“…Palladium-catalyzed cross-couplings with aryl bromides and resin-bound amines have also been described. [307][308] In addition, on-resin intramolecular reactions to give indo- lines were reported for MBHA resin (67-84% yields, Scheme 36). 309 Schultz and co-workers employed palladium-catalyzed cross-couplings between resin-bound heteroaryl chlorides and amines/anilines as the final diversification step in the SPS of a library of kinase inhibitors on a BAL-type resin (78-89% yields).…”

Section: Scheme 35mentioning

confidence: 99%

N-Alkylation Reactions and Indirect Formation of Amino Functionalities in Solid-Phase Synthesis

Olsen¹,

Franzyk²,

Jaroszewski³

2005

Synthesis

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Aliphatic and aromatic amino functionalities are present in a wide variety of natural products and drugs, as well as in synthetic small molecular probes with therapeutic and/or diagnostic potential in drug discovery. As solid-phase synthesis and combinatorial chemistry have emerged as important tools for generation of compound libraries, development of broad-scope and efficient chemistry for the introduction of various functional groups into resinanchored substrates is highly important. Herein, we present a review of the literature concerning formation of the amino functionality on solid phase.

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“…[11][12][13] Ferrocene (Fc, Figure 1) as well as its derivatives, as important organometallic compounds, is commonly applied in material science, catalysis, and synthetic organic chemistry. [14][15][16] Fc-β-CD, as the first example of second sphere coordination complexes of CDs with organometallic compounds, was reported in 1984. 17 Since then, there have been many reports on the formation and characterization on CD complexes of Fc analogues.…”

Section: Introductionmentioning

confidence: 98%

“…Ferrocene (Fc, Figure ) as well as its derivatives, as important organometallic compounds, is commonly applied in material science, catalysis, and synthetic organic chemistry. – Fc−β-CD, as the first example of second sphere coordination complexes of CDs with organometallic compounds, was reported in 1984 . Since then, there have been many reports on the formation and characterization on CD complexes of Fc analogues. – A recent study delineates our efforts to elucidate the correlation between the destruction of a second sphere complex through the release of its members and the separate destruction of its members based on the relationship between heating temperatures and fragment compositions of the complex …”

Section: Introductionmentioning

confidence: 99%

Formation, Characterization, and Thermal Degradation Behavior of a Novel Tricomponent Aggregate of β-Cyclodextrin, Ferrocene, and Polypropylene Glycol

Song

Guo

et al. 2010

J. Phys. Chem. B

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A tricomponent aggregate PPG-Fc-beta-CD formed by polypropylene glycol (PPG), ferrocene (Fc), and beta-cyclodextrin (beta-CD) was obtained and characterized by a series of physical methods, such as (1)H nuclear magnetic resonance, flame atomic absorption spectrometry, high performance liquid chromatography, UV-vis absorption spectroscopy, thermogravimetry, and gas chromatography coupled to time-of-flight mass spectrometry. First, the tricomponent aggregate exhibited a component ratio of 1:28:32 (PPG/Fc/beta-CD) in the solid state, and showed a completely different order in thermal stability when compared with beta-CD: under a nitrogen atmosphere, beta-CD > PPG-Fc-beta-CD, and in a vacuum, PPG-Fc-beta-CD > beta-CD. Second, the appearance of two peculiar points p and q at the end of TG curve of the aggregate gave a strong impression that the degradation rate further increased after the sharp decomposition of the aggregate reached point p and the amount present in the residual fraction at point q about 780.0 K was lower than 1%, both of which were rather different from those reported previously. This finding implied that the molecular assembly resulting from the binding interaction among Fc, PPG, and beta-CD induced more efficiently the degradation of each of them. Third, an interesting phenomenon was found that the order of thermal release of the three assembled components in PPG-Fc-beta-CD was Fc > beta-CD > PPG. Results of this study provide some insight into an initial attempt to construct a supramolecule among a polymer, a coordination compound, and an organic compound.

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Solid-Phase Synthesis of N-Bi- and N-Terarylpiperazines via Three Different and Consecutive Palladium-Catalyzed Cross-Coupling Reactions

Abstract: Novel nonsymmetrical N-bi- and N-terarylpiperazines were synthesized on solid phase via three consecutive palladium-catalyzed cross-coupling reactions in which C-N, C-B, and C-C bonds are formed consecutively.

Cited by 8 publications

References 23 publications

Comprehensive Survey of Combinatorial Library Synthesis: 2004

Comprehensive Survey of Combinatorial Library Synthesis: 2004

N-Alkylation Reactions and Indirect Formation of Amino Functionalities in Solid-Phase Synthesis

Formation, Characterization, and Thermal Degradation Behavior of a Novel Tricomponent Aggregate of β-Cyclodextrin, Ferrocene, and Polypropylene Glycol

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