85891-82-3Relevant academic research and scientific papers
Unexpected extension of usage of PPh3/CBr4, a versatile reagent: Isomerization of aromatic allylic alcohols
Gong, Wanchun,Liu, Yun,Xue, Jijun,Xie, Zhixiang,Li, Ying
supporting information, p. 1597 - 1599 (2013/02/23)
The PPh3/CBr4-catalyzed isomerization of 2-aromatic allylic alcohols into the corresponding saturated aldehydes or ketones has been achieved at room temperature in good to excellent yields under mild and metal-free conditions. This new methodology has been applied successfully to the synthesis of ibuprofen in four steps.
Synthesis of 3-Methyl-5,6-dihydro-3H-benzofuroisoquinolin-7(7aH)-ones
Weller, Dwight D.,Stirchak, Eugene P.,Weller, Doreen L.
, p. 4597 - 4605 (2007/10/02)
The coupling of 2-(alkoxymethoxy)phenylcopper derivatives with the salt of ethyl chloroformate and ethyl 3-(pyridin-3-yl)propenoate was found to be an efficient method for the preparation of 4-(2-hydroxyphenyl)pyridines 13 substituted at C-3 with a propanoate side chain.N-Methylation and O-alkylation with ethyl bromoacetate gave salts 3 which when treated with base underwent an intramolecular enolate addition to the pyridinium nucleus to produce spiro 4.Prolonged base treatment of 4 yielded ethyl 3-methyl-7-hydroxy-5,7a-dihydro-3H-benzofuroisoquinoline-6-carboxylates 5 by a Dieckmann reaction.Reduction of 5 led to predominately trans-3-methylhexahydro-1H-benzofuroisoquinolin-7(7aH)-ones, while reduction of 4 and then Dieckmann cyclization yielded mainly the cis isomers.
SYNTHESIS OF 3-METHYL-2,3,4,4a,5,6-HEXAHYDRO-1H-BENZOFUROISOQUINOLINE-7(7aH)-ONES
Weller, Dwight, D.,Weller, Doreen, L.
, p. 5239 - 5242 (2007/10/02)
The 2,3,4,4a,5,6-hexahydro-1H-benzofuroisoquinoline-7(7aH)-one ring system is prepared from a 4-arylpyridine precursor by sequential intramolecular enolate addition to a pyridinium ion, Dieckmann cyclization, and catalytic hydrogenation.
