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Interaction of 4‐Oxo‐4 H ‐pyrazolo[5,1‐ c ][1,2,4]triazin‐1‐ides with Grignard Reagents
Author(s) -
Ivanov Sergey M.,
Shestopalov Anatoliy M.
Publication year - 2018
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.3236
Subject(s) - chemistry , reactivity (psychology) , nucleophile , triazine , selectivity , reagent , medicinal chemistry , magnesium , nucleophilic substitution , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
Reactions of magnesium 3‐ tert ‐butyl‐8‐ R ‐4‐oxo‐4 H ‐pyrazolo[5,1‐ c ][1,2,4]triazin‐1‐ides (R = CN, CO 2 Et) with AlkMgBr led to nucleophilic additions to either side chain or triazine core, with selectivity being dependent on the nature of substituents, as well as on the solvents used. Previously inaccessible C 8 ‐functionalized and C 4 ‐functionalized pyrazolo[5,1‐ c ][1,2,4]triazines and 3‐ tert ‐butyl‐3‐ethyl‐4‐oxo‐1,2,3,4‐tetrahydropyrazolo[5,1‐ c ][1,2,4]triazine were synthesized, and their reactivity and spectral data discussed.