Mark York

article

The 3-substitution of naphthalene-1,2-diones with boronic acids: a C–H functionalization approach to novel spirooxazine photochromics

Mark York

Tetrahedron Letters > 2012 > 53 > 17 > 2226-2230

The addition of alkyl and aryl boronic acids to naphthalene-1,2-diones in the presence of an excess of ammonium persulfate and catalytic silver nitrate to yield 3-functionalized naphthalene-1,2-diones is reported. The products of these reactions were then further processed to yield the corresponding novel spirooxazine photochromic dyes.

article

A continuous-flow synthesis of annulated and polysubstituted furans from the reaction of ketones and α-haloketones

Mark York

Tetrahedron Letters > 2011 > 52 > 47 > 6267-6270

A synthesis of di-, tri- and tetra-substituted furans from reaction of the corresponding ketones and α-haloketones with LiHMDS is reported. Reaction under continuous-flow conditions gave increased yields and removed the need for external cooling when compared to the unoptimised batch conditions.

article

Optimisation of 6-substituted isoquinolin-1-amine based ROCK-I inhibitors

Peter Ray, Jane Wright, Julia Adam, Sylviane Boucharens, more

Bioorganic & Medicinal Chemistry Letters > 2011 > 21 > 4 > 1084-1088

Rho kinase is an important target implicated in a variety of cardiovascular diseases. Herein, we report the optimisation of the fragment derived ATP-competitive ROCK inhibitors 1 and 2 into lead compound 14A. The initial goal of improving ROCK-I potency relative to 1, whilst maintaining a good PK profile, was achieved through removal of the aminoisoquinoline basic centre. Lead 14A was equipotent against...

article

Design, synthesis, and structure–activity relationship study of bicyclic piperazine analogs of indole-3-carboxamides as novel cannabinoid CB1 receptor agonists

Elizabeth M. Moir, Kazuya Yoshiizumi, Jim Cairns, Phillip Cowley, more

Bioorganic & Medicinal Chemistry Letters > 2010 > 20 > 24 > 7327-7330

Bicyclic piperazine derivatives were synthesized as conformationally constrained analogs of N-alkyl piperazines and were found to be potent CB1 receptor agonists. The CB1 receptor agonist activity was dependent upon the absolute configuration of the chiral center of the bicyclic ring system. Although the conformational constraint did not protect the compounds from metabolism by N-dealkylation, several...

article

Controlling Molecular Mobility in Polymer Matrices: Synchronizing Switching Speeds of Multiple Photochromic Dyes

Nino Malic, Jonathan A. Campbell, Abdelselam S. Ali, Mark York, more

Macromolecules > 2010 > 43 > 20 > 8488 - 8501

article

The use of polyhedral oligomeric silsesquioxane (POSS) as a soluble support for organic synthesis: A case study with a POSS-bound isocyanate scavenger reagent

Mark York, Richard A. Evans

Tetrahedron Letters > 2010 > 51 > 35 > 4677-4680

The use of polyhedral oligomeric silsesquioxane (POSS) as a soluble support in organic synthesis is reported. A POSS-bound isocyanate was readily synthesised in one step from commercially available starting materials and was isolated in high yield and purity by simple filtration. It was found to perform well as a scavenger for excess amine in the solution phase synthesis of amides and sulfonamides,...

article

Design, synthesis, and structure–activity relationship study of conformationally constrained analogs of indole-3-carboxamides as novel CB1 cannabinoid receptor agonists

Takao Kiyoi, Mark York, Stuart Francis, Darren Edwards, more

Bioorganic & Medicinal Chemistry Letters > 2010 > 20 > 16 > 4918-4921

Novel tricyclic indole-3-carboxamides were synthesized as structurally restricted analogs of bicyclic indoles, and found to be potent CB1 cannabinoid receptor agonists. The CB1 agonist activity depended on the absolute configuration of the chiral center of the tricyclic ring. The preferred enantiomer was more potent than the structurally unconstrained lead compound. Structure–activity relationships...

article

Synthesis and properties of 1,3,3-trimethylspiro[indoline-2,3′-naphtho[2,1-b][1,4]oxazin]-6′-amine, a novel, red colouring photochromic spirooxazine

Mark York, Richard A. Evans

Tetrahedron Letters > 2010 > 51 > 16 > 2195-2197

The synthesis and photochromic properties of 1,3,3-trimethylspiro[indoline-2,3′-naphtho[2,1-b][1,4]oxazin]-6′-amine, a novel red-colouring photochromic spirooxazine and derivatives is reported. The synthesis proceeds via an unusual one-pot transamination, oxime formation, N–O bond cleavage, spirooxazine formation process.

article

Investigation of the scope of a [3+2] cycloaddition approach to isoxazole boronic esters

Jane E. Moore, Mark W. Davies, Katharine M. Goodenough, Robert A.J. Wybrow, more

Tetrahedron > 2005 > 61 > 28 > 6707-6714

The [3+2] cycloaddition reaction of nitrile oxides and alkynylboronates provides direct access to a wide variety of isoxazole boronic esters. Specifically, this technique has been employed to generate trisubstituted isoxazole 4-boronates and disubstituted isoxazoles where the boronic ester moiety can be installed at C-4 or C-5 with high levels of regiocontrol. The application of this methodology in...

article

Reagent concentration effects in the REM resin solid phase synthesis of tertiary amines

J. Richard Morphy, Zoran Rankovic, Mark York

Tetrahedron > 2003 > 59 > 12 > 2137-2145

The use of reagent concentration has resulted in increased rates for all stages of the REM resin synthesis of tertiary amines. These increases in rate translate into faster reaction times, higher yields and lower reagent consumption. Of the methods examined, the most successful was the use of perfluorous solvents, either alone or with a small amount of organic co-solvent.

article

One-pot Hofmann elimination–transesterification/amidation reactions on REM resin using perfluorous solvents

J.Richard Morphy, Zoran Rankovic, Mark York

Tetrahedron Letters > 2002 > 43 > 36 > 6413-6415

The incorporation of 2,2,2-trifluoroethanol esters into substrates for the REM resin synthesis of 3° amines allows a one-pot Hofmann elimination/transesterification protocol to be performed. In this way α-amino acid esters and amides were synthesised by adding alcohols or 1° amines to the Hofmann elimination mixture. The excess of nucleophile required to drive the transesterification or amidation...

article

Low dilution procedures in solid-phase organic synthesis: Diels–Alder and Heck reactions

J.Richard Morphy, Zoran Rankovic, Mark York

Tetrahedron Letters > 2002 > 43 > 34 > 5973-5975

The use of extremely low solvent volumes (2 μL or less per mg resin) results in significant increases in yield for both the Diels–Alder and Heck reactions on solid-phase compared to standard high dilution techniques.

article

Optimization of Reaction Conditions for REM Resin-Bound Quaternization Reactions

Kenneth S. Cameron, J. Richard Morphy, Zoran Rankovic, Mark York

Journal of Combinatorial Chemistry > 2002 > 4 > 3 > 199 - 203

article

Fluorocarbon accelerated supported transformations (FAST) on REM resin

J. Richard Morphy, Zoran Rankovic, Mark York

Tetrahedron Letters > 2001 > 42 > 42 > 7509 - 7511

The use of perfluorous organic solvents in the solid-phase synthesis of 3 ^o amines on REM resin allows a large reduction in both reaction time and the amount of amine required for a successful Michael reaction. Yields of products were typically at least three fold greater than those observed with standard solvents under the same conditions.

article

Bimetallic catalytic cascade ring closing metathesis-intramolecular Heck reactions using a fluorous biphasic solvent system or a polymer-supported palladium catalyst

Ronald Grigg, Mark York

Tetrahedron Letters > 2000 > 41 > 37 > 7255-7258

The combination of ring closing metathesis and intramolecular Heck reactions in a cascade gives bridged ring systems in good yield. Two methods using either a fluorous biphasic solvent system or a polymer-supported palladium catalyst overcome the observed incompatibility of the catalysts.

article

Ring closing metathesis reactions of isoquinoline and β-carboline enamines

Paul Evans, Ronald Grigg, Mark York

Tetrahedron Letters > 2000 > 41 > 20 > 3967-3970

Ring closing metathesis of enamines derived from isoquinolines and β-carboline occurs in DCM at room temperature in good yields. The products of ring closing metathesis bear close structural relationships to many alkaloidal natural products and are obtained in yields that bear approximate inverse proportionality to the calculated basicity of the enamine starting material.

article

Sequential and Cascade Palladium Catalysed Cyclisation-Anion Capture-Olefin Metathesis

Paul Evans, Ronald Grigg, M. Imran Ramzan, Visuvanathar Sridharan, more

Tetrahedron Letters > 1999 > 40 > 15 > 3021-3024

The sequential or cascade combination of palladium catalysed cascade cyclisation-anion capture involving two- and three-component processes with olefin metathesis, provides access to fused and spirocyclic ring systems in good yield and a bridged ring forming sequence is reported.

article

Sequential and Cascade Olefin Metathesis - Intramolecular Heck Reaction

Ronald Grigg, Visuvanathan Sridharan, Mark York

Tetrahedron Letters > 1998 > 39 > 23 > 4139-4142

The sequential or cascade combination of olefin metathesis with intramolecular Heck reactions provides access to fused-, bridged- and spiro-cyclic ring systems in good yield.

INFONA - science communication portal

Search results for: Mark York

The 3-substitution of naphthalene-1,2-diones with boronic acids: a C–H functionalization approach to novel spirooxazine photochromics

A continuous-flow synthesis of annulated and polysubstituted furans from the reaction of ketones and α-haloketones

Optimisation of 6-substituted isoquinolin-1-amine based ROCK-I inhibitors

Design, synthesis, and structure–activity relationship study of bicyclic piperazine analogs of indole-3-carboxamides as novel cannabinoid CB1 receptor agonists

Controlling Molecular Mobility in Polymer Matrices: Synchronizing Switching Speeds of Multiple Photochromic Dyes

The use of polyhedral oligomeric silsesquioxane (POSS) as a soluble support for organic synthesis: A case study with a POSS-bound isocyanate scavenger reagent

Design, synthesis, and structure–activity relationship study of conformationally constrained analogs of indole-3-carboxamides as novel CB1 cannabinoid receptor agonists

Synthesis and properties of 1,3,3-trimethylspiro[indoline-2,3′-naphtho[2,1-b][1,4]oxazin]-6′-amine, a novel, red colouring photochromic spirooxazine

Investigation of the scope of a [3+2] cycloaddition approach to isoxazole boronic esters

Reagent concentration effects in the REM resin solid phase synthesis of tertiary amines

One-pot Hofmann elimination–transesterification/amidation reactions on REM resin using perfluorous solvents

Low dilution procedures in solid-phase organic synthesis: Diels–Alder and Heck reactions

Optimization of Reaction Conditions for REM Resin-Bound Quaternization Reactions

Fluorocarbon accelerated supported transformations (FAST) on REM resin

Bimetallic catalytic cascade ring closing metathesis-intramolecular Heck reactions using a fluorous biphasic solvent system or a polymer-supported palladium catalyst

Ring closing metathesis reactions of isoquinoline and β-carboline enamines

Sequential and Cascade Palladium Catalysed Cyclisation-Anion Capture-Olefin Metathesis

Sequential and Cascade Olefin Metathesis - Intramolecular Heck Reaction

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