On the reaction of o-functional benzylmalononitriles with N-bisnucleophiles as well as alcoholates

Article abstract of DOI:10.1002/ardp.19933261105

The o-functional benzylmalononitriles 1, 16 and 22 show different reactivity towards N-bisnucleophiles and alcoholates. 16 and 22 cyclize with guanidine to the pyrimidinetriamines 17 and 23 only while compound 1 provides 4 by a twofold ring closure. 1 reacts with hydrazine and ethylendiamine to afford the 2-benzazepines 7 and 12, respectively. Refluxing compound 22 with Na-methylate or Na-ethylate, respectively, leads to the 2-benzazepine-cyanoenolether 26a,b. Analogous reactions with 16 did not succeed in cyclization.