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On triazoles. XXV . The reaction of methyl (5‐amino‐3‐Q‐1 H ‐1,2,4‐triazolyl)dithiocarbonates with amines
Author(s) -
Barkóczy József,
Reiter József
Publication year - 1991
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.5570280624
Subject(s) - chemistry , thiazoline , thiazole , ring (chemistry) , derivative (finance) , closure (psychology) , thiazine , stereochemistry , medicinal chemistry , organic chemistry , market economy , financial economics , economics
Different “functionalised” triazolylthioamides 3 and ‐thioureas 4 were synthesised. The ring closure of the ω‐hydroxyalkylthioamides 3/2–5 led to the corresponding 2‐thiazoline 5/2–4 and 5,6‐dihydro‐4 H ‐1,3‐thiazine 5/5 derivatives, respectively. Unexpectedly, the ring closure of the corresponding 2,2‐dimethoxyethyl derivative 3/18 led depending on the reaction conditions to a thiazole derivative 6 or to its 1,2,4‐triazolo[3,4‐ b ]‐1,3,5‐triazepin‐5(9 H )‐thione isomer 7 representing a novel ring system. To corroborate its structure 7 was methylated to the corresponding S ‐methyl derivative 8 . Spectroscopical evidence is given for the structure of derivatives 3–8 obtained.