ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
An examination of the BISCHLER-NAPIERALSKI 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 5H-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 LiAlH4, 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.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19640470508
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