Authors: IAROSLAV BAGLAI, VALERIE MARAVAL, ZOIA VSEVOLODIVNA VOITENKO, CARINE DUHAYON, YULIAN MIHAILOVICH VOLOVENKO, REMI CHAUVIN
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 (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-(3-methyl-4-oxo-3,4-dihydroquinazolin-2-yl)benzoate as an oxidation side product.
Keywords: Isoindoles, methylation processes, oxidative ring opening, quinazolines
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