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Selective mono, bis, and trisiminoformylation of 2,4,6‐trialkyl‐1,3,5‐triazines ‐ unusual enol acylenamine tautomerism of hydroxyalkenyl‐1,3,5‐triazines
Author(s) -
Schulz HansJoachim,
Liebscher Jürgen,
Luger Peter,
Quian Minxie,
Mulzer Johann
Publication year - 1992
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.5570290515
Subject(s) - chemistry , tautomer , enol , keto–enol tautomerism , medicinal chemistry , organic chemistry , catalysis
2,4,6‐Trialkyl‐1,3,5‐triazines 1 can selectively be mono, bis or trisiminoformylated by reaction with trismorpholinomethane 2 or chloromethylene iminium salts 3 (Vilsmeier reagents), with each alkyl substituent reacting with only one molecule of the electrophile. The resulting aminoalkenyltriazines 4, 5 and 6 are partially or fully hydrolysed to corresponding formylation products. The latter exist either in enol or in unusual acylenamine tautomeric structures 10, 12 , and 13 , depending on the number of enamine or enol units found in the molecule. Reaction of triazines 1 with chlorobenzylidene iminium salts 16 gives monoiminobenzoylation to enaminotriazines 17 .