64097-56-9Relevant articles and documents
Aminomethylation de l'homoacridane, de l'iminodibenzyle et de l'iminostilbene
Lehuede, Jacques,Vierfond, Jean-Michel,Miocque, Marcel
, p. 185 - 191 (2007/10/02)
The aminomethylation of 6,11-dihydro-5H-dibenzoazepine (HA), 10,11-dihydro-5H-dibenzoazepine (IDB) and dibenzoazepine (ISB) was studied in order to evaluate modifications of antidepressive activities of these tricyclic structures.By reaction with formalin and a secondary amine in ethanol medium acidified by means of acetic acid, homoacridane (HA) leads to a monosubstitution product on carbone 2 (yield 50percent).Iminodibenzyl (IDB) and iminostilbene (ISB) also give monoaminomethylation products in analogous position (yields are respectively 74 and 59percent).In each case, the optimum amount of acetic acid has been determined.If acetic acid is used as the solvent, diaminomethylation is observed in positions 2 and 8 (yiels are 74percent for IDB and 59percent for ISB).Structures of the isolated products have been studied by IR and 1H nmr.The postulated mechanism of aromatic electrophilic substitution is discussed with respect to various factors: differences in basicities of heterocyclic amines; electronic structures and nitrogen activation of aromatic tricyclic systems; influence of amount of acetic acid on salification equilibria.