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Synthesis of nitrogen‐containing heterocycles. 4. A facile route to new 1, 2, 4‐triazole derivatives
Author(s) -
Miyamoto Yoshiko,
Yamazaki Chiji
Publication year - 1989
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.5570260347
Subject(s) - chemistry , ketone , alkyl , pyrimidine , nitrogen , medicinal chemistry , alkane , triazole , organic chemistry , 1,2,4 triazole , stereochemistry , catalysis
The reaction of amino‐ N (4), N (4)‐dimethylaminornethylenehydrazones 1 of some aliphatic carbonyl compounds with ethyl ethoxymethylenecyanoacetate 2 gave directly symmetrical gem ‐bis(3‐dimethylamino‐1, 2, 4‐triazol‐1‐yl)alkanes 4 and (3‐dimethylamino‐1, 2, 4‐triazol‐1‐yl)alkenes 5 at room temperature, with the former being major product. On the other hand, the reaction of amino‐ N (4)‐methylaminomethylenehydrazone homologue 1 of aliphatic ketone with 2 gave ethyl 2‐alkyl‐5‐methylamino[1, 2, 4]triazolo[1, 5‐ c ]pyrimidine‐8‐carboxylate 7 as the only product with elimination of alkane.