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

doi:10.1016/0040-4020(96)00486-3

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

Departament de Química

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Resum

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.

Idioma original	Anglès
Pàgines (de-a)	9521-9534
Revista	Tetrahedron
Volum	52
Número	28
DOIs	https://doi.org/10.1016/0040-4020(96)00486-3
Estat de la publicació	Publicada - 8 de jul. 1996

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10.1016/0040-4020(96)00486-3

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@article{cb88fe83ea6b41dbbce3c56fbbc07ac1,

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

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.",

author = "Catherine Goux and Silvana Sigismondi and Denis Sinou and Montserrat P{\'e}rez and Marcial Moreno-Ma{\~n}as and Roser Pleixats and Merc{\`e} Villarroya",

year = "1996",

month = jul,

day = "8",

doi = "10.1016/0040-4020(96)00486-3",

language = "English",

volume = "52",

pages = "9521--9534",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "28",

}

TY - JOUR

T1 - Palladium(0)-catalysed allylation of uracils and thiouracils. Influence of the solvent on the regioselectivity of the allylation

AU - Goux, Catherine

AU - Sigismondi, Silvana

AU - Sinou, Denis

AU - Pérez, Montserrat

AU - Moreno-Mañas, Marcial

AU - Pleixats, Roser

AU - Villarroya, Mercè

PY - 1996/7/8

Y1 - 1996/7/8

N2 - 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.

AB - 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.

U2 - 10.1016/0040-4020(96)00486-3

DO - 10.1016/0040-4020(96)00486-3

M3 - Article

SN - 0040-4020

VL - 52

SP - 9521

EP - 9534

JO - Tetrahedron

JF - Tetrahedron

IS - 28

ER -

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

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