13580-93-3Relevant articles and documents
A novel domino synthesis of quinazolinediones by palladium-catalyzed double carbonylation
Li, Haoquan,Li, Wanfang,Spannenberg, Anke,Baumann, Wolfgang,Neumann, Helfried,Beller, Matthias,Wu, Xiao-Feng
supporting information, p. 8541 - 8544 (2014/07/21)
Combining commercially available bromoanilines and bromobenzonitriles in a novel double carbonylation process allows for a straightforward synthesis of isoindolo[1,2-b]quinazoline-10,12-diones. At least five different C-C and/or C-N bonds are selectively formed in this 3-component reaction, which likely proceeds through sequential carbonylation-cyclization-isomerisation- carbonylation steps. Notably, two molecules of CO are inserted in this highly efficient palladium-catalyzed process.
NMR STUDIES ON IMIDINES. II. 1H AND 13C NUCLEAR MAGNETIC RESONANCE STUDY ON THE TAUTOMERISM AND GEOMETRICAL ISOMERISM OF 3-ARYLIMINOISOINDOLINONES.
Spiessens, Luc I.,Anteunis, J. O.
, p. 763 - 790 (2007/10/02)
3-Aryliminoisoindolinones 2 have been fully examined by 1H and 13C NMR spectroscopy.A complete analysis of 13C-1H coupling constant is given for three of the compounds (2c, 3a, 4b).Only the arrylimino tautomeric forms are presented in polar (DMSO-d6,; CD3OD) and apolar solvent (CDCl3) as established by comparaison of 1H and 13C NMR chemical shift values of 2 with those of suitable model compounds (3, 4, 6 and 7).It is shown that both the endo- and exocyclic N-methylated aryliminoisoindol(en)inones (3 and 4) adopt the E configuration (due to steric hidrance of the N-methyl group) but that the title compounds are present in solution as 4:1 mixtures of Z and E components (Figure 4).This is not the case for the 2'-pyridyl derivatives (2c, 2e, 2f) where the Z form benefits from an intramolecular hydrogen bond.An interesting proximity 13C chemical shift effect is produced by the variation in steric crowding in the E vs Z isomers of the title compounds.
