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Reactivity of nucleophilic uracil derivatives
Author(s) -
Grangier Géraldine,
Aitken David J.,
Guillaume Dominique,
Husson HenriPhilippe,
Tomas Alain,
Viossat Bernard
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.5570310673
Subject(s) - chemistry , carbanion , reactivity (psychology) , nitrile , electrophile , alkylation , nucleophile , uracil , tricyclic , methylene , bromide , benzyl bromide , medicinal chemistry , organic chemistry , catalysis , medicine , dna , biochemistry , alternative medicine , pathology
The reactivity of uracil derivatives bearing acidic methylene groups at N1 was investigated. On treatment with strong base, compounds with nitrile as the activating group underwent extensive dimerisation to give new tricyclic systems. Ester‐activated compounds also produced dimers in the absence of an external electrophile, but their monomeric carbanions could be trapped by prompt addition of benzyl bromide to give normally alkylated products.