On the reactivity of isoindolo[2,1-a]quinazoline-5-ones |
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Authors: | Zoia V Voitenko Oleksandr I Halaev Sergey V Kolotilov Christine Lepetit Bruno Donnadieu Remi Chauvin |
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Institution: | a Kiev National Taras Shevchenko University, 60 Volodymyrska St, 01033 Kiev, Ukraine b L.V.Pisarzhevskii Institute of Physical Chemistry of NAS, pr. Nauki 31, Kiev, Ukraine c CNRS, LCC (Laboratoire de Chimie de Coordination), 205, route de Narbonne, F-31077 Toulouse, France d Université de Toulouse, UPS, INPT, LCC, F-31077 Toulouse, France |
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Abstract: | Base- and acid-catalyzed nucleophilic addition of 11H-isoindolo2,1-a]quinazoline-5-one to aromatic aldehydes and maleimides was investigated. The aldol adducts and condensation products were obtained stereoselectively. Main diastereomers of the Michael adducts were isolated in 74-89% yield, and converted by N-methylation to new stable α-substituted isoindole derivatives, for which 6-methylisoindolo2,1-a]]quinazoline-5-one stands as the unsubstituted reference. The stability of the latter was monitored in moist aerated CDCl3 solution, and one of the oxidative hydrolysis product was characterized by X-ray diffraction analysis as the corresponding N-arylphthalimide. The reactivity of the unsubstituted 6-methylisoindolo2,1-a]]quinazoline-5-one was also investigated with acetylenic Michael acceptors. Fully conjugated isoindole derivatives possessing an original pull-push-pull structure were obtained. The conformations and molecular orbitals of the dibenzoylacetylene adduct were studied at the DFT level of theory. Its static quadratic hyperpolarizabilty β0 was also calculated at the ZINDO level. |
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Keywords: | Acceptor-donor-acceptor chromophores Aldol condensation Aromatic aldehydes Dibenzoylacetylene Isoindoles Isoindolo[2 1-a]quinazolines Maleimides Michael addition Quadratic hyperpolarizability |
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