Regioselective formation of N-alkyl-3,5-pyrazole derived ligands. A synthetic and computational study

Vanessa Montoya; Josefina Pons; Vicenç Branchadell; Josep Ros

doi:10.1016/j.tet.2005.09.085

Regioselective formation of N-alkyl-3,5-pyrazole derived ligands. A synthetic and computational study

Vanessa Montoya, Josefina Pons, Vicenç Branchadell, Josep Ros

Departament de Química

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New N-alkyl-3,5-pyrazole derived ligands were synthesized by reaction between 3,5-pyrazole derived ligands and the appropriate haloalkane in toluene or THF using NaOEt or NaH as base. When the precursor ligand bears a pyridyl substituent the alkylation reaction presents a large regioselectivity. Theoretical calculations have been carried out to rationalize the experimental observations. It has been shown that regioselectivity is governed by the formation of Na+-pyrazolide chelate complexes. © 2005 Elsevier Ltd. All rights reserved.

Idioma original	Anglès
Pàgines (de-a)	12377-12385
Revista	Tetrahedron
Volum	61
Número	52
DOIs	https://doi.org/10.1016/j.tet.2005.09.085
Estat de la publicació	Publicada - 26 de des. 2005

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10.1016/j.tet.2005.09.085

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title = "Regioselective formation of N-alkyl-3,5-pyrazole derived ligands. A synthetic and computational study",

abstract = "New N-alkyl-3,5-pyrazole derived ligands were synthesized by reaction between 3,5-pyrazole derived ligands and the appropriate haloalkane in toluene or THF using NaOEt or NaH as base. When the precursor ligand bears a pyridyl substituent the alkylation reaction presents a large regioselectivity. Theoretical calculations have been carried out to rationalize the experimental observations. It has been shown that regioselectivity is governed by the formation of Na+-pyrazolide chelate complexes. {\textcopyright} 2005 Elsevier Ltd. All rights reserved.",

keywords = "N-alkyl-3,5-pyrazole derived ligands, N-alkylation, Regioisomers",

author = "Vanessa Montoya and Josefina Pons and Vicen{\c c} Branchadell and Josep Ros",

year = "2005",

month = dec,

day = "26",

doi = "10.1016/j.tet.2005.09.085",

language = "English",

volume = "61",

pages = "12377--12385",

journal = "Tetrahedron",

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T1 - Regioselective formation of N-alkyl-3,5-pyrazole derived ligands. A synthetic and computational study

AU - Montoya, Vanessa

AU - Pons, Josefina

AU - Branchadell, Vicenç

AU - Ros, Josep

PY - 2005/12/26

Y1 - 2005/12/26

N2 - New N-alkyl-3,5-pyrazole derived ligands were synthesized by reaction between 3,5-pyrazole derived ligands and the appropriate haloalkane in toluene or THF using NaOEt or NaH as base. When the precursor ligand bears a pyridyl substituent the alkylation reaction presents a large regioselectivity. Theoretical calculations have been carried out to rationalize the experimental observations. It has been shown that regioselectivity is governed by the formation of Na+-pyrazolide chelate complexes. © 2005 Elsevier Ltd. All rights reserved.

AB - New N-alkyl-3,5-pyrazole derived ligands were synthesized by reaction between 3,5-pyrazole derived ligands and the appropriate haloalkane in toluene or THF using NaOEt or NaH as base. When the precursor ligand bears a pyridyl substituent the alkylation reaction presents a large regioselectivity. Theoretical calculations have been carried out to rationalize the experimental observations. It has been shown that regioselectivity is governed by the formation of Na+-pyrazolide chelate complexes. © 2005 Elsevier Ltd. All rights reserved.

KW - N-alkyl-3,5-pyrazole derived ligands

KW - N-alkylation

KW - Regioisomers

U2 - 10.1016/j.tet.2005.09.085

DO - 10.1016/j.tet.2005.09.085

M3 - Article

SN - 0040-4020

VL - 61

SP - 12377

EP - 12385

JO - Tetrahedron

JF - Tetrahedron

IS - 52

ER -

Regioselective formation of N-alkyl-3,5-pyrazole derived ligands. A synthetic and computational study

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