ChemInform Abstract: Chemistry of Functionalized Benzazepines. Part 5. Synthesis and Chemical Transformation of the 1,2,4,5-Tetrahydrospiro[3H-2-benzazepine-3,1′-cycloalkanes].

✍ Scribed by V. KOUZNETSOV; A. PALMA R; S. SALAS; L. Y. VARGAS; F. ZUBKOV; A. VARLAMOV; J. R. MARTINEZ

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 39 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199813141

✦ Synopsis

Chemistry of Functionalized Benzazepines.

Part 5. Synthesis and Chemical Transformation of the 1,2,4,5-Tetrahydrospiro[3H-2benzazepine-3,1'-cycloalkanes].

-A number of new spiroderivatives of tetrahydro-2-benzazepine (III) are synthesized by reaction of imines (I) with allyl Grignard reagent (II) and subsequent cyclization. Nitration and bromination of (III) take place regioselectively on position C-8 of the phenyl ring giving (IV) and (V), respectively. Alkylation and acylation provides the corresponding N-substituted derivatives (VII) and (IX), respectively. Oxidation of (IIIa) with Na 2 WO 4 /H 2 O 2 affords the novel nitrone (X). -(KOUZNETSOV, V.;