On the peculiar reactivity of a C,N-annelated isoindole core

Authors : İaroslav BAGLAI, Valérie MARAVAL, Zoia Vsevolodivna VOITENKO

Pages : 121-126

Doi:10.3906/kim-1306-58

View : 15 | Download : 7

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :C-, N-, and/or O-methylation products were generated from 11H-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 insert ignore into journalissuearticles values(MeI); leads mainly to the C,C-dimethylated product 11,11-dimethyl-11H-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-insert ignore into journalissuearticles values(3-methyl-4-oxo-3,4-dihydroquinazolin-2-yl);benzoate as an oxidation side product.
Keywords : Isoindoles, methylation processes, oxidative ring opening, quinazolines