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Ringschlussreaktionen des Butadiendioxids mit Hydrazinen zu neuen Derivaten des Pyrazolidins und Piperidazins
Author(s) -
Meyer H. R.,
Gabler R.
Publication year - 1963
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19630460727
Subject(s) - chemistry , ring (chemistry) , hydrazine (antidepressant) , adduct , medicinal chemistry , stereochemistry , organic chemistry , chromatography
The reaction of butadiene dioxide (dl‐and meso ‐) with various hydrazines led to 1: 1‐adducts having either pyrazolidine or piperidazine structures. Using N,N′‐di‐substituted hydrazines, pyrazolidine derivatives were obtained with yields of 70–80%, whereas hydrazine itself reacted with DL‐butadiene dioxide to give about 20% of trans ‐4,5‐dihydroxypiperidazine and a small quantity of trans ‐7,8‐tetrahydroxy‐10‐azaquinolizidine. The five ring closure reaction seems to be a general and preparativeloy interesting pyrazolidine synthesis. The structure of a representative of the 5‐ and of the 6‐ring system was proven by their conversion into open chain diamines. The constitutions of these diamines were established by independent synthesis or by conversion into known compounds. The assignation of the other 1: 1‐adducts to the pyrazolidine or to the piperidzaien series respectively was carried out by mean of NMR‐analysis.