Paper
Synthetic utilization of polynitroaromatic compounds. 6. Remarkable regioselectivity in nucleophilic displacement of aromatic nitro groups with amines.
Published Feb 27, 2008 · K. A. Kislyi, A. V. Samet, Yu. A. Strelenko
The Journal of organic chemistry
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Abstract
5,7-Dinitroquinazoline-4-ones undergo nucleophilic displacement of a nitro group with N-, S-, and O-nucleophiles. In contrast to previously studied dinitro-substituted benzoannulated five- and seven-membered heterocycles (where a high degree of selectivity was observed), these quinazolines mostly yield mixtures of regioisomeric substitution products. At the same time, primary and secondary amines react selectively to afford 5-aminoquinazolones (peri-substitution). A similar effect is observed for some other polynitroaromatic compounds with adjacent nitro and carbonyl groups. This phenomenon is attributed to a stabilization of the intermediate peri-sigma-complex by intramolecular hydrogen bond N(+)-H...O double bond C.
This study demonstrates remarkable regioselectivity in nucleophilic displacement of aromatic nitro groups with amines, resulting in mixtures of regioisomeric substitution products while primary and secondary amines react selectively to afford 5-aminoquinazolones.
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