Premium
Study of the pyrimidine nucleobase C5C6 bond reactivity under thio‐michael/aldol tandem reaction conditions
Author(s) -
Velez Edna Vázquez,
Desnous Céline,
Clivio Pascale
Publication year - 2006
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.5570430442
Subject(s) - chemistry , aldol reaction , michael reaction , adduct , nucleobase , pyrimidine , thymine , intramolecular force , thio , context (archaeology) , reactivity (psychology) , stereochemistry , tandem , conjugate , dna , organic chemistry , catalysis , biochemistry , medicine , paleontology , mathematical analysis , materials science , alternative medicine , mathematics , pathology , composite material , biology
Pyrimidine nucleobases can undergo a Michael/aldol tandem reaction triggered by a thiolate. In an intramolecular context, 5′‐deoxy‐2′,3′‐isopropylidene‐5′‐thiouridine affords the reminiscent Baylis‐Hillman adduct after retro‐Michael addition whereas its thymine counterpart is unreactive. In an intermolecular context, the conjugate addition‐aldol reaction occurs only if the C5C6 double bond is activated.