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

Department of Chemistry

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

23 Citations (Scopus)

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. © 2005 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	12377-12385
Journal	Tetrahedron
Volume	61
Issue number	52
DOIs	https://doi.org/10.1016/j.tet.2005.09.085
Publication status	Published - 26 Dec 2005

Keywords

N-alkyl-3,5-pyrazole derived ligands
N-alkylation
Regioisomers

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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.",

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

year = "2005",

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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

VL - 61

SP - 12377

EP - 12385

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 52

ER -