914642-03-8Relevant articles and documents
Synthetic utilization of polynitroaromatic compounds. 6. Remarkable regioselectivity in nucleophilic displacement of aromatic nitro groups with amines
Kislyi, Konstantine A.,Samet, Alexander V.,Strelenko, Yuri A.,Semenov, Victor V.
, p. 2285 - 2291 (2008/09/18)
(Chemical Equation Presented) 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-σ-complex by intramolecular hydrogen bond N+-H...O=C.