Palladium-catalyzed allylation of pyrimidine-2,4-diones (uracils) and of 6-membered heterocyclic ambident sulfur nucleophiles

Marcial Moreno-Mañas; Roser Pleixats; Mercè Villarroya

doi:10.1016/S0040-4020(01)90197-8

Palladium-catalyzed allylation of pyrimidine-2,4-diones (uracils) and of 6-membered heterocyclic ambident sulfur nucleophiles

Marcial Moreno-Mañas, Roser Pleixats, Mercè Villarroya

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

39 Citations (Scopus)

Abstract

Pd(0)-Catalyzed allylation of six-membered ambident heterocycles bearing NH-CO, NH-CS and CH2-CO moieties obey the regioselectivity rules: C>O; N> S>N; NH-CO>NH-CS. Uracil and 5-methyluracil (thymine) do not show regioselectivity (N-1 = N-3) whereas 6-methyluracil is regioselectively allylated at N-3 (N-3>N-1). © 1993.

Original language	English
Pages (from-to)	1457-1464
Journal	Tetrahedron
Volume	49
Issue number	7
DOIs	https://doi.org/10.1016/S0040-4020(01)90197-8
Publication status	Published - 12 Feb 1993

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Moreno-Mañas, M., Pleixats, R., & Villarroya, M. (1993). Palladium-catalyzed allylation of pyrimidine-2,4-diones (uracils) and of 6-membered heterocyclic ambident sulfur nucleophiles. Tetrahedron, 49(7), 1457-1464. https://doi.org/10.1016/S0040-4020(01)90197-8

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abstract = "Pd(0)-Catalyzed allylation of six-membered ambident heterocycles bearing NH-CO, NH-CS and CH2-CO moieties obey the regioselectivity rules: C>O; N> S>N; NH-CO>NH-CS. Uracil and 5-methyluracil (thymine) do not show regioselectivity (N-1 = N-3) whereas 6-methyluracil is regioselectively allylated at N-3 (N-3>N-1). {\textcopyright} 1993.",

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AB - Pd(0)-Catalyzed allylation of six-membered ambident heterocycles bearing NH-CO, NH-CS and CH2-CO moieties obey the regioselectivity rules: C>O; N> S>N; NH-CO>NH-CS. Uracil and 5-methyluracil (thymine) do not show regioselectivity (N-1 = N-3) whereas 6-methyluracil is regioselectively allylated at N-3 (N-3>N-1). © 1993.

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DO - 10.1016/S0040-4020(01)90197-8

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