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6‐ and 7‐aryl‐1,2,4‐triazolo[4,3‐ b ]‐1,2,4‐triazines. Synthesis and characterization
Author(s) -
Trust Ronald I.,
Albright J. Donald,
Lovell F. M.,
Perkinson N. A.
Publication year - 1979
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.5570160721
Subject(s) - aryl , chemistry , regioselectivity , derivative (finance) , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , alkyl , financial economics , economics
Synthetic methods for the preparation of 6‐aryl‐1,2,4‐triazolo[4,3‐ b ]‐1,2,4‐triazines ( 1 ) and the 7‐aryl isomers ( 2 ) are described. Compounds 1 were prepared from aryl glyoxaldoximes 76 via 6‐aryl‐1,2,4‐triazin‐3(2 H )ones ( 75 ). A simple procedure for the preparation of the 7‐aryl isomers was effected using arylglyoxals 11 and the triazoles ( 4, 12a and 12b ). However, complete regioselectivity was not realized in all cases, especially when the triazoles were substituted at the C‐5 position. A regiospecific synthesis of the 7‐aryl isomers 2 was developed via the 3‐methylthio‐5‐aryl‐1,2,4‐triazines ( 61 ). The structure of the parent 6‐phenyl derivative 5 was confirmed by x‐ray crystallography.