102696-70-8Relevant articles and documents
Competitive formation of β-amino acids, propenoic, and ylidenemalonic acids by the Rodionov reaction from malonic acid, aldehydes, and ammonium acetate in alcoholic medium
Lebedev,Lebedeva,Sheludyakov,Kovaleva,Ustinova,Kozhevnikov
, p. 1113 - 1124 (2005)
The Rodionov reaction of 49 available aliphatic and aromatic aldehydes with malonic acid and ammonium acetate in alcoholic medium, resulting in formation of β-amino acids, propenoic, and ylidenemalonic acids, was studied. Certain regioselectivity regularities of the reaction were revealed. Among the variety of ketones studied, cyclohexanone is the only whose reaction yields a β-amino acid. Unusual dehydrofluorination of 6-chloro-2-fluorocinnamic acid under the Rodionov reaction was discovered. 2005 Pleiades Publishing, Inc.
Design, synthesis and pharmacobiological evaluation of novel acrylic acid derivatives acting as lipoxygenase and cyclooxygenase-1 inhibitors with antioxidant and anti-inflammatory activities
Pontiki, Eleni,Hadjipavlou-Litina, Dimitra,Litinas, Konstantinos,Nicolotti, Orazio,Carotti, Angelo
experimental part, p. 191 - 200 (2011/02/27)
A series of novel acrylic acid derivatives bearing at the 3 position thienyl, furfuryl and 3,5-ditert-butyl-4-hydroxyphenyl substituents have been designed, synthesized and tested as potential dual lipoxygenase/cyclooxygenase-1 (LOX/COX-1) inhibitors and
Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 10. Generation of 2-methylstyrylalkynes and their thermal cyclisation to 2-alkenylnaphthalenes
Aitken, R. Alan,Boeters, Christine,Morrison, John J.
, p. 2625 - 2631 (2007/10/03)
A series of nine 2-methylcinnamoyl phosphorus ylides 7 have been prepared and are found upon FVP at 500°C to undergo loss of Ph3PO to afford the corresponding styrylalkynes 8 whose fully assigned 13C NMR spectra are presented. FVP of the ylides at 900°C leads to cyclisation to give substituted naphthalenes 9-18; the mechanism of these reactions may proceed either by initial hydrogen atom loss or an initial [1,7]hydrogen shift, but an alternative route involving an initial [1,3]hydrogen shift has been ruled out by examination of a deuterium labelled analogue. For the α-phenyl ylides 7d and 7i a further cyclisation leads to benzo[c]fluorene derivatives and this process has been extended to a thiophene analogue to give fluoreno[3,4-b]thiophene. The formation of 2-ethylnaphthalene as the main product from the α-methoxycarbonyl ylide 7e is due to a secondary thermal reaction of methyl 2-naphthylacetate which may involve a radical chain reaction featuring, as the propagation step, an unusual homolytic substitution at a methoxy carbon by a 2-naphthylmethyl radical.
