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Synthesis of 1,4,6,7‐tetrahydroimidazo[2,1‐ c ] [1,2,4] triazines
Author(s) -
Eberle Marcel K.,
Schirm Paul
Publication year - 1977
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.5570140111
Subject(s) - chemistry , methylhydrazine , hydrazine (antidepressant) , salt (chemistry) , medicinal chemistry , triazine , combinatorial chemistry , organic chemistry , stereochemistry , chromatography , phenylhydrazine
From 2‐methylthioimidazoline and phenaeylbromides in DMF there were obtained the 2‐(2‐methylthio‐2‐imidazolin‐1‐yl)aeetopht'nones 3a‐3f . From these the substituted 3‐phenyl‐1,4,6,7‐tetrahytlroimidazo[2,1‐ c ][1,2,4]triazines 4a‐4n were prepared upon reaction with hydrazine and methylhydrazine respectively. Compound 4a was degraded to the triazine 6. From the (2‐methylthio‐2‐imidazolin‐l‐yl)‐acetie acid ester 10, the imidazo[2,1‐ c ] [1,2,4]triazines 11a‐11c were prepared. Selective ethylation on the oxygen was achieved with 11b in the presence of Meerwein' salt.