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A convenient synthesis of substituted piperazines via aminomercuration‐demercuration of diallylamines
Author(s) -
Barluenga J.,
Nájera C.,
Yus M.
Publication year - 1980
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570170515
Subject(s) - chemistry , sodium borohydride , steric effects , stereoselectivity , bromide , medicinal chemistry , vinyl bromide , potassium bromide , aryl , organic chemistry , stereochemistry , catalysis , alkyl
cis and trans ‐2,6‐ Bis [bromomercuriomethyl]piperazines II which bear equal or different substituents at each nitrogen are obtained in the reaction of N ‐substituted diallylamines with mercury(II) acetate and aryl‐amines followed by a double decomposition process with potassium bromide. Their reduction with sodium borohydride lead to the corresponding 1,4‐disubstituted cis ‐ and trans ‐2,6‐dimethylpiperazines III. Steric factors account for the remarkable stereoselectivity observed in the preparation of compounds IIIi‐IIIn in which a 3:1 cis to trans isomer ratio is found.
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