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Synthesis of 2‐hydroxy‐2‐phenylethylamino derivatives as potential α‐adrenergic blocking agents
Author(s) -
Alvarez M.,
Granados R.,
Lavilla R.,
Salas M.
Publication year - 1985
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.5570220326
Subject(s) - chemistry , thiazolidine , cystamine , condensation , stereochemistry , ring (chemistry) , hydrochloride , epoxide , organic chemistry , combinatorial chemistry , biochemistry , catalysis , physics , thermodynamics
The synthesis of N,N'‐bis[6‐(2‐hydroxy‐2‐phenylethylamino)hexyl] cystamines 4 , and N‐(2‐hydroxy‐2‐phenylethyl)‐1,6‐hexanediamines 6 are described. Compounds 4 were obtained by condensation of the requisite epoxide 2 with 3‐(6‐aminohexyl)‐1,3‐thiazolidine followed by dimerization with opening of the thiazolidine ring. A similar method was used for the preparation of compounds 6. In order to prepare 4j (N,N'‐bis{6‐[2‐hydroxy‐2(3,4‐dihydroxyphenyl)ethylamino]hexyl}cystamine), several procedures were tested; the method of choice involved the use of 3,4‐dihydroxybenzaldehyde with both hydroxy groups protected as methoxymethyl ethers.