Archiv der Pharmazie p. 865 - 869 (1993)
Update date:2022-08-04
Topics:
Troschutz
Grun
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.
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Doi:10.1021/ja00082a006
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