Palladium(0)-catalysed allylation of uracils and thiouracils. Influence of the solvent on the regioselectivity of the allylation

Catherine Goux, Silvana Sigismondi, Denis Sinou, Montserrat Pérez, Marcial Moreno-Mañas, Roser Pleixats, Mercè Villarroya

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24 Citations (Scopus)

Abstract

Uracil and 5-substituted uracils are monoallylated at N-1 in H2O- CH3CN with the catalytic systemPd(OAc)2/P(C6H4-m -SO3Na)3 (or tppts) although performing the reaction in H2O/THF with the system Pd2(dba)3/dppb leads to diallylations at N-1 + N-3.2-Thiouracil, 5-methyl-2-thiouracil (2- thiothymine) and 6-methyl-2-thiouracil are monoallylated at sulfur in H2O/CH3CN with the catalytic system Pd(OAc)2/P(C6H4-m-SO3Na)3 (or tppts). Performing the reactions in H2O/THF with the system Pd2(dba)3/dppb leads to diallylations at N-1 + N-3 of 2-thiouracil and 2-thiothymine whereas 6-methyl-2-thiouracil is diallylated at S + N-3.
Original languageEnglish
Pages (from-to)9521-9534
JournalTetrahedron
Volume52
Issue number28
DOIs
Publication statusPublished - 8 Jul 1996

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