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Reaction of 3‐amino‐5,6‐dimethyl‐1,2,4‐triazine with electrophiles
Author(s) -
Suzuki Toshinobu,
Okazaki Masahiko,
Mitsuhashi Keiryo
Publication year - 1986
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.5570230354
Subject(s) - chemistry , electrophile , triethylamine , aryl , triazine , medicinal chemistry , organic chemistry , catalysis , alkyl
The title compound was reacted with four types of electrophiles and the respective reaction sites were investigated. The reaction with aryl isocyanates in the conventional way yielded the corresponding ureas. In the presence of triethylamine, the 3‐amino group was diacylated with acyl chlorides. On the other hand, in the cases with arylsulfonyl chlorides and p ‐nitrobenzaldehyde under similar conditions, the methyl group at 5‐position was preferentially attacked to give arylsulfonylmethyl and p ‐nitrostyryl derivatives, respectively.