Browsing by Author "Cunningham, Desmond"
Now showing items 1-8 of 8
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1,3-dipolar character of 2-vinyl quinazoline 3-oxides; first and second generation cycloaddition products
Heaney, Frances; Lawless, Elaine; Mahon, Mary; McArdle, Patrick; Cunningham, Desmond (Royal Society of Chemistry (RSC), 2006-01-01)The reaction between the heteroaromatic N-oxides 1a, 1b and 1c with dimethyl acetylenedicarboxylate or methyl propiolate furnishes 1,3-benzodiazepines, the products of ring transformations of primarily formed cycloadducts. ... -
Preparation of imidazo[1,2-c]pyrimidinones from a chloropyrimidine and an electron poor ω-allylic amine
Heaney, Frances; Bourke, Sharon; Burke, Cathriona; Cunningham, Desmond; McArdle, Patrick (Royal Society of Chemistry (RSC), 1998-01-01)Synthesis of the title ring system by a sequential intermolecular nucleophilic displacement and intramolecular 'conjugate' addition has been achieved both as a one pot and as a stepwise procedure; an X-ray structure ... -
Pyrimidine annelated heterocycles - synthesis and cycloaddition of the first pyrimido[1,4]diazepine n-oxides
Heaney, Frances; Burke, Cathriona; Cunningham, Desmond; McArdle, Patrick (Royal Society of Chemistry (RSC), 2001-01-01)5-Formyl- and 5-acetyl-4-(alkenylamino)pyrimidines 5 have been prepared as precursors to novel pyrimido[1,4]diazepine N-oxides 3. In addition to cyclisation to the targeted dipoles the substrates 5 have also been observed ... -
Simultaneous double 1,3-dipolar cycloaddition reactions involving bisnitrones or bisdipolarophiles. 1h nmr investigation of the conformational preferences of n-methyl- and n-phenyl-isoxazolidines
Heaney, Frances; Rooney, Oliver; Cunningham, Desmond; McArdle, Patrick (Royal Society of Chemistry (RSC), 2001-01-01)Binitrones 1a and 1b reacted with N-methylmaleimide giving bisisoxazolidines. Diastereospecific reaction of the phenyl substituted dipole 1a gave 3a whilst the N-methyl dipole 1b furnished diastereomeric adducts 3b, 4 and ... -
Site selectivity in the addition of ketoximes to activated allenes and alkynes; n- versus o-alkylation
Heaney, Frances; Kelly, Bronwyn M.; Bourke, Sharon; Rooney, Oliver; Cunningham, Desmond; McArdle, Patrick (Royal Society of Chemistry (RSC), 1999-01-01)Reaction of ketoximes with methyl propiolate afforded geometrical isomers of the methyl 3-(hydroxyimino)propanoates 4 and of the O-vinyl oximes 5 as well as the 2-isoxazoline 6. With dimethyl penta-2,3-diendioate 8c reaction ... -
Steric control of reactivity: formation of oximes, benzodiazepinone n-oxides and isoxazoloquinolinones
Heaney, Frances; Bourke, Sharon; Cunningham, Desmond; McArdle, Patrick (Royal Society of Chemistry (RSC), 1998-01-01)Reaction of the alkenyl carbonyl compounds 1 with hydroxylamine can lead to the formation of the oximes 2, the benzodiazepinone N-oxides 3 or the isoxazoloquinolinones 5. The product(s) of reaction are shown to depend on ... -
Α-keto amides as precursors to heterocycles—generation and cycloaddition reactions of piperazin-5-one nitrones
Heaney, Frances; Fenlon, Julie; McArdle, Patrick; Cunningham, Desmond (Royal Society of Chemistry (RSC), 2003-03-10)alpha-Keto amides 10a,b, formed from reaction of pyruvic or benzoylformic acid with allyl amine are found to present as single rotameric forms whilst their tertiary amido analogues 10c,d present as two rotamers in solution ... -
Α-oximono-esters as precursors to heterocycles – generation of oxazinone n-oxides and cycloaddition to alkene dipolarophiles
Heaney, Frances; Fenlon, Julie; O′Mahony, Colm; McArdle, Patrick; Cunningham, Desmond (Royal Society of Chemistry (RSC), 2003-01-01)Preparation of a series of terminally and internally substituted delta-alkenyl and delta-alkynyl esters 6,7 and 9, potential precursors to oxazin-2-one nitrones, has been attempted. Condensation between pyruvic or benzoylformic ...