Insertion of arynes into the carbon-oxygen double bond of amides and its application into the sequential reactions
The reaction of arynes, generated from ortho-(trimethylsilyl)aryl triflates, with the CO bond of formamides gave salicylaldehyde derivatives via the formation of formal [2+2] adducts. The sequential transformation of arynes into ortho-disubstituted arenes, o-aminoalkylphenols or o-hydroxyalkylphenols, was achieved by one-pot procedure using dialkylzincs.
Yoshioka, Eito,Miyabe, Hideto
experimental part
p. 179 - 189
(2012/02/15)
SYNTHESIS AND CONFIGURATION OF SOME NEW BICYCLIC 3-ARYLIDENE- AND 3-HETEROARYLIDENE-2-OXINDOLES
The synthesis of a novel class of bicyclic 3-arylidene- and 3-heteroarylidene-2-oxindoles possessing tyrosine kinase inhibitory activity is described.Compounds 1-16 have been prepared by condensation of 2-oxindole with a (hetero)aromatic aldehyde belonging to the naphthalene, tetralin, quinoline or indole series.The compounds so obtained were single E or Z isomers or separable mixtures thereof.The single E or Z isomers could be partially transformed into their isomers by acid or basic catalysis.The E/Z configuration assignment was achieved by 1H NMR spectroscopy on the basis of chemical shifts and NOE data obtained from NOESY spectra.
Buzzetti, Franco,Pinciroli, Vittorio,Brasca, M. Gabriella,Crugnola, Angelo,Fustinoni, Silvia,Longo, Antonio
p. 69 - 76
(2007/10/02)
PHOTOCHEMICAL REACTION OF NAPHTHYL α-NITROACRYLATES
Photolysis of 2-nitro-3-(1-naphthyl)acrylates (1) in acetone gave novel naphthofuran-2-carboxylates (2) and 2-(alkoxyoxalylamino-methylene)naphthalen-1-ones (3). 2-Nitro-3-(2-naphthyl)acrylate also produced the furan derivative 2 on irradiation.A mechanism for this new photorearrangement reaction is described.KEYWORDS -- photochemical rearrangement; naphthyl α-nitroacrylate; naphtholfuran-2-carboxylate; 2-(ethoxyoxalylaminomethylene)naphthalen-1-one; α-keto-β-hydroxyiminoester