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Synthesis of new v ‐triazolopyrimidinium salts
Author(s) -
Bátori S.,
Messmer A.
Publication year - 1994
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.5570310458
Subject(s) - chemistry , ketone , yield (engineering) , reagent , medicinal chemistry , grignard reaction , organic chemistry , materials science , metallurgy
New v ‐triazolo[1,5‐α]‐ and v ‐triazolo[1,5‐ c ]pyrimidinium salts 12a‐e, 13a‐c have been synthesized via oxidation ( i.e. cyclodehydrogenation) of the appropriate pyrimidyl ketone arylhydrazones 3a‐e, 6a‐c using TBB (2,4,4,6‐tetrabromocyclohexa‐2,5‐dien‐1‐one) as the reagent. The arylhydrazones were obtained by standard reactions; the Grignard reaction of 2‐cyano‐ and 4‐cyanopyrimidine 1a,b, 4a‐c gave 2‐pyrimidyl‐ and 4‐pyrimidyl ketones 2a‐e, 5a‐c , which reacted with arylhydrazines to yield the desired ketone arylhydrazones 3a‐e, 6a‐c.