Synthesis and Reactivity Profile of Ylidenemalononitrile Enamines and Their Ester Analogs Towards Electrophiles and Nucleophiles
Herein, we describe the synthesis and reactivity of enamines derived from ylidenemalononitriles and ylidenecyanoacetates. The enamine scope was expanded by (1) increasing yields of aldehyde-derived ylidenemalononitriles, (2) incorporating silyl functional
Longstreet, Ashley R.,Rivalti, Daniel,McQuade, D. Tyler
p. 8583 - 8596
(2015/09/15)
Improved synthesis of mono- and disubstituted 2-halonicotinonitriles from alkylidene malononitriles
Pyridines with 2,3,4 and/or 5 substitution remain challenging to prepare. Existing strategies to form multisubstituted 2-halonicotinonitriles via enamines suffer from dimerization of the starting alkylidene malononitriles resulting in low yields. Through alteration of reaction conditions, a new high yielding method into enamines was realized by condensing DMF-DMA and alkylidene malononitriles in the presence of substoichiometric acetic anhydride. Cyclization of the resulting enamines under Pinner conditions provided 2-halonicotinonitriles in high overall yields.
Longstreet, Ashley R.,Campbell, Brian S.,Gupton, B. Frank,McQuade, D. Tyler
supporting information
p. 5298 - 5301
(2013/11/06)
DIRECT SUBSTITUTION OF A METHOXY GROUP BY BROMINE IN 2-METHOXYPYRIDINE-3-CARBONITRILES: A SYNTHESIS OF 2-BROMOPYRIDINE-3-CARBONITRILES
The treatment of a wide variety of 2-methoxypyridine-3-carbonitriles with phosphorus oxytribromide in the presence of pyridinium hydrobromide and phosphoric acid yields directly the corresponding pyridine system in which the methoxy group has been substit
Victory, P.,Borrell, J. I.,Castejon, P.,Martinez-Teipel, B.,Vidal-Ferran, A.
Novel substituted (3-loweralkylamino-2-R1 O-propoxy)pyridines, their pharmaceutically acceptable salts, certain intermediates and their preparation are disclosed. These pyridines have pharmaceutically useful properties such as β-adrenergic blocking activity.
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(2008/06/13)
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