ON THE REACTION OF O-FUNCTIONAL BENZYLMAL ONONITRILES WITH N-BISNUCLEOPHILES AS WELL AS ALCOHOLATES

Authors
TROSCHUTZ R GRUN L
Citation
R. Troschutz et L. Grun, ON THE REACTION OF O-FUNCTIONAL BENZYLMAL ONONITRILES WITH N-BISNUCLEOPHILES AS WELL AS ALCOHOLATES, Archiv der pharmazie, 326(11), 1993, pp. 865-869
Citations number
8
Categorie Soggetti
Chemistry,"Pharmacology & Pharmacy
Journal title
Archiv der pharmazie → ACNP
ISSN journal
03656233
Volume
326
Issue
11
Year of publication
1993
Pages
865 - 869
Database
ISI
SICI code
0365-6233(1993)326:11<865:OTROOB>2.0.ZU;2-V
Abstract
The o-functional benzylmalononitriles 1, 16 and 22 show different reac tivity towards N-bisnucleophiles and alcoholates. 16 and 22 cyclize wi th guanidine to the pyrimidinetriamines 17 and 23 only while compound 1 provides 4 by a twofold ring closure. L reacts with hydrazine and et hylendiamine to afford the 2-benzazepines 7 and 12, respectively. Refl uxing compound 22 with Na-methylate or Na-ethylate, respectively, lead s to the 2-benzazepine-cyanoenolether 26a,b. Analogous reactions with 16 did nor succeed in cyclization.