13580-93-3Relevant academic research and scientific papers
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.
Structure, polymorphism and thermal properties of phenyliminoisoindolines
Zhang, Zhi-Qin,Uth, Samnang,Sandman, Daniel J.,Foxman, Bruce M.
, p. 769 - 776 (2007/10/03)
The crystal and molecular structures of (a) 1-imino-3-phenyliminoisoindoline (2), (b) two polymorphs (3Mono and 3Tric) and a nexane solvate (3Hex) of 1,3-bis(phenylimino)isoindoline (3) and (c) 3-phenyliminoisoindolinone (4) were determined via single-crystal x-ray diffraction. The two polymorphs and solvate of 3 were all obtained by crystallization from hexane. In the solid state, 2 is found as the anti isomer of the amino tautomer, and all forms of 3 exist as either the syn,anti or anti,anti isomers of the diimino tautomer. The 3Tric and 3Mono polymorphs represent a rare example in which the phenomena of conformational polymorphism and conformational isomorphism occur for the same substance. Compound 4 crystallizes as the anti isomer of the keto form. Differential scanning calorimetry and thermogravimetric analysis were performed to characterize the thermal properties of samples of 2-4. X-ray powder diffraction studies on 2, 3 and 4 reveal that, whereas specimens of 2 are a single phase, none of the samples of 3 and 4 crystallize as single phases under the conditions of the experiments. Copyright
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.
