52487-41-9Relevant academic research and scientific papers
An anti-tetraamination of a 1,3-diene unit via cascade annulations of the azulenone scaffold with dicarbonyl azo-compounds
Ishigaki, Yuhei,Mahendar, Velisoju,Oguri, Hiroki,Oikawa, Hideaki
, p. 3304 - 3305 (2010)
Dense and stereo-controlled integrations of C-N bonds on the azulenone scaffold are achieved by sequential (i) ene, (ii) [6+2]-cycloaddition, and (iii) hetero-conjugate addition reactions leading to a topologically complex bis-bridged skeleton.
New results in homoheptalene chemistry
Rueedi, Georg,Hansen, Hans-Juergen
, p. 1017 - 1047 (2007/10/03)
The thermal reaction of homoazulene (= bicyclo[5.3.1]undeca-1,3,5,7,9-pentaene; 2) with dimethyl acetylenedicarboxylate (ADM) in 1,2-dichloroethane (ClCH2CH2Cl) results, in contrast to an earlier report [5], in formation of not only
Selective bond cleavage of [5.3.1]propellanes by lead tetraacetate: A facile entry into the carbocyclic frame [A,B ring] of taxol
Kumar, Pradeep,Rao, Ashok T.,Saravanan,Pandey, Bipin
, p. 3397 - 3400 (2007/10/02)
[5.3.1]Propellanes e.g., the tricyclo[5.3.1.01,7]undeca-2,4-dien-10-one 8 and the corresponding methylidene compound 10 were prepared from methyl cinnamate 2 in several steps involving rhodium(II) acetate mediated cyclization of 4 to 6 as a key step. The selective central cyclopropyl bond cleavage in 8 and 10 by lead tetraacetate provides the basis of a new approach to the construction of carbocylic frame of A,B ring of Taxol.
The Intramolecular Buchner Reaction of Aryl Diazoketones. Substituent Effects and Scope in Synthesis
Kennedy, Michael,McKervey, M. Anthony,Maguire, Anita R.,Tuladhar, Sarbajna M.,Twohig, M. Fiona
, p. 1047 - 1054 (2007/10/02)
Rhodium(II) acetate-catalysed cyclisation of α-diazoketones derived from 3-arylpropionic acid produces bicyclodecatrienones or 2-tetralones depending on the substitution pattern of the aryl ring in the precursor; the former products are transformed into the latter catalytically with trifluoroacetic acid.Precursors with methyl, methoxy, and acetoxy substituents have been examined, efficient cyclisation occurring in all cases.When the precursor contains a meta-methoxy substituent, 2-tetralones are obtained directly.The efficient conversion of 3-phenylpropionicacid into trans-1-methylbicyclodecan-2-one is also described, partial asymmetric synthesis having been realised through the use of rhodium (S)-mandelate as the cyclisation catalyst.Cyclisations of diazoketones derived from 4-phenylbutyric acid and 5-phenylpentanoic acid have also been studied; the former provides a new entry into the bicycloundecane system whereas the latter produces a 2,3-disubstituted cyclopentanone via C-H insertion.Aspects of the cycloheptatriene-norcaradiene equilibrium in fused ring systems are discussed.
Efficient Synthesis of Bicyclodecatrienones and of 2-Tetralones via Rhodium(II) Acetate-catalysed Cyclisation of α-Diazoketones derived from 3-Arylpropionic Acids
McKervey, M. Anthony,Tuladhar, Sarbajna M.,Twohig, M. Fiona
, p. 129 - 130 (2007/10/02)
Rhodium(II) acetate-catalysed cyclisation of α-diazoketones derived from 3-arylpropionic acids produces bicyclodecatrienones or 2-tetralones depending on the substitution pattern of the aryl ring; the former products are transformed into the latter by catalytic amounts of trifluoroacetic acid.
A Short New Azulene Synthesis
Scott, Lawrence T.,Minton, Mark A.,Kirms, Mark A.
, p. 6311 - 6314 (2007/10/02)
A short new azulene synthesis requiring no dehydrogenation step, has been developed (Scheme 1).Intramolecular carbene addition creates the bicyclic ring system of azulene with a high degree of unsaturation and versatile functionality in a single step from a simple benzene derivative.The synthesis is particularly amenable to preparation of specific 13C- and 2H-labeled azulenes.
