Author/Authors :
BAGLAI, Iaroslav University of Toulouse, France , BAGLAI, Iaroslav Centre National de la Recherche Scientifique (CNRS) - LCC (Laboratoire de Chimie de Coordination), France , BAGLAI, Iaroslav Kiev National Taras Shevchenko University, Ukraine , MARAVAL, Valérie Centre National de la Recherche Scientifique (CNRS) - LCC (Laboratoire de Chimie de Coordination), France , MARAVAL, Valérie University of Toulouse, France , VOITENKO, Zoia Vsevolodivna Kiev National Taras Shevchenko University, Ukraine , DUHAYON, Carine Centre National de la Recherche Scientifique (CNRS) - LCC (Laboratoire de Chimie de Coordination), France , DUHAYON, Carine University of Toulouse, France , VOLOVENKO, Yulian Mikhailovich Kiev National Taras Shevchenko University, Ukraine , CHAUVIN, Remi Centre National de la Recherche Scientifique (CNRS) - LCC (Laboratoire de Chimie de Coordination), France , CHAUVIN, Remi University of Toulouse, France
Abstract :
C-, N-, and/or O-methylation products were generated from 11 H-isoindolo[2,1-a]quinazoline-5-one upon treatment with NaH followed by iodomethane under air, and possible recrystallization from methanol. Two products were fully characterized by NMR and X-ray diffraction analysis. In accordance with the HSAB principle, this soft methylating agent (MeI) leads mainly to the C,C-dimethylated product 11,11-dimethyl-11 H -isoindolo[2,1-a]quinazoline- 5-one, which was previously not observed, beside the N-methylated product, in a procedure using methyl tosylate as a hard methylating agent of the same substrate in the initial absence of a base. A mechanism is finally proposed for the formation of methyl 2-(3-methyl-4-oxo-3,4-dihydroquinazolin-2-yl)benzoate as an oxidation side product.
Keywords :
Isoindoles , methylation processes , oxidative ring opening , quinazolines
