Dibenzo‐azepine, ‐diazepine, ‐Oxazepine und ‐thiazepine. 3. Mitteilung über siebengliedrige Heterocyclen
1964; Wiley; Volume: 47; Issue: 5 Linguagem: Inglês
10.1002/hlca.19640470508
ISSN1522-2675
AutoresF. Hunziker, F. Künzle, O. Schindler, J. Schmutz,
Tópico(s)Coordination Chemistry and Organometallics
ResumoAbstract An examination of the B ISCHLER ‐N APIERALSKI reaction starting with 2‐acylamino‐diphenyl‐amines, ‐sulfides, ‐methanes, and ethers, resp., is reported. Using phosphorous oxychloride or polyphosphoric acid, the products are azomethine derivatives of 5 H ‐dibenzo[b, e]‐1,4‐diazepines, dibenzo[b, f]‐l,4‐thiazepines, llH‐dibenzo[b, e]‐azepines resp. dibenzo[b, f]‐l, 4‐oxazepines having the general formula III. The azomethine bridge in III can be hydrogenated catalytically or reduced with LiAlH 4 , to give derivatives of the general formula VI. Using several dialkylaminoalkyl chlorides in the presence of Na‐amide, these derivatives are alkylated to VII. The basic strengths of several derivatives of III and VI are reported and the correlation between the basicity and the heteroatom in III and VI is discussed. The thiazepine derivatives show a noticeably lowered basicity, which we could not explain either by the inductive or by mesomeric effects of the sulfur bridge‐atom.
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