An efficient method for the construction of phenolic compounds incorporating pendant amine arms

Febee R. Louka; Zahra Haghighijoo; Ayush A. Deshpande; Carl Didier; Aline Fady; Roland C. Fischer; Ana Torvisco; Franz A. Mautner; Nahed M.H. Salem; Salah S. Massoud

doi:10.1016/j.ica.2024.122027

An efficient method for the construction of phenolic compounds incorporating pendant amine arms

Febee R. Louka^*, Zahra Haghighijoo, Ayush A. Deshpande, Carl Didier, Aline Fady, Roland C. Fischer, Ana Torvisco, Franz A. Mautner, Nahed M.H. Salem, Salah S. Massoud

^*Corresponding author for this work

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

Abstract

A new series of tripodal and linear phenolic-amines as well as 1,4,7,10-tetrakis(2,4-dialky-1-hydroxy-6-benzyl)-1,4,7,10-tetraazacyclododecane were efficiently synthesized in excellent to reasonably moderate yields. The one-pot reactions were performed in methanol solution through the commercially available 2,4-disubstited-phenols and dialkyldiamines or the macrocycles 1,4,7,10-tetraazacyclododecane (cyclen) and 1,4,8,11-tetraazacyclotetradecane (cyclam) in the presence of aqueous 37 % HCHO and Et₃N. All the isolated compounds were spectroscopically characterized and, in some cases, structurally determined by single crystal- X-ray crystallography.

Original language	English
Article number	122027
Journal	Inorganica Chimica Acta
Volume	566
DOIs	https://doi.org/10.1016/j.ica.2024.122027
Publication status	Published - 1 Jun 2024

Keywords

Mass spectroscopy
Phenolic amines
Phenolic ligands
Tripod ligands
X-Ray

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.ica.2024.122027

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title = "An efficient method for the construction of phenolic compounds incorporating pendant amine arms",

abstract = "A new series of tripodal and linear phenolic-amines as well as 1,4,7,10-tetrakis(2,4-dialky-1-hydroxy-6-benzyl)-1,4,7,10-tetraazacyclododecane were efficiently synthesized in excellent to reasonably moderate yields. The one-pot reactions were performed in methanol solution through the commercially available 2,4-disubstited-phenols and dialkyldiamines or the macrocycles 1,4,7,10-tetraazacyclododecane (cyclen) and 1,4,8,11-tetraazacyclotetradecane (cyclam) in the presence of aqueous 37 % HCHO and Et3N. All the isolated compounds were spectroscopically characterized and, in some cases, structurally determined by single crystal- X-ray crystallography.",

keywords = "Mass spectroscopy, Phenolic amines, Phenolic ligands, Tripod ligands, X-Ray",

author = "Louka, {Febee R.} and Zahra Haghighijoo and Deshpande, {Ayush A.} and Carl Didier and Aline Fady and Fischer, {Roland C.} and Ana Torvisco and Mautner, {Franz A.} and Salem, {Nahed M.H.} and Massoud, {Salah S.}",

note = "Publisher Copyright: {\textcopyright} 2024 Elsevier B.V.",

year = "2024",

month = jun,

day = "1",

doi = "10.1016/j.ica.2024.122027",

language = "English",

volume = "566",

journal = "Inorganica Chimica Acta",

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T1 - An efficient method for the construction of phenolic compounds incorporating pendant amine arms

AU - Louka, Febee R.

AU - Haghighijoo, Zahra

AU - Deshpande, Ayush A.

AU - Didier, Carl

AU - Fady, Aline

AU - Fischer, Roland C.

AU - Torvisco, Ana

AU - Mautner, Franz A.

AU - Salem, Nahed M.H.

AU - Massoud, Salah S.

PY - 2024/6/1

Y1 - 2024/6/1

N2 - A new series of tripodal and linear phenolic-amines as well as 1,4,7,10-tetrakis(2,4-dialky-1-hydroxy-6-benzyl)-1,4,7,10-tetraazacyclododecane were efficiently synthesized in excellent to reasonably moderate yields. The one-pot reactions were performed in methanol solution through the commercially available 2,4-disubstited-phenols and dialkyldiamines or the macrocycles 1,4,7,10-tetraazacyclododecane (cyclen) and 1,4,8,11-tetraazacyclotetradecane (cyclam) in the presence of aqueous 37 % HCHO and Et3N. All the isolated compounds were spectroscopically characterized and, in some cases, structurally determined by single crystal- X-ray crystallography.

AB - A new series of tripodal and linear phenolic-amines as well as 1,4,7,10-tetrakis(2,4-dialky-1-hydroxy-6-benzyl)-1,4,7,10-tetraazacyclododecane were efficiently synthesized in excellent to reasonably moderate yields. The one-pot reactions were performed in methanol solution through the commercially available 2,4-disubstited-phenols and dialkyldiamines or the macrocycles 1,4,7,10-tetraazacyclododecane (cyclen) and 1,4,8,11-tetraazacyclotetradecane (cyclam) in the presence of aqueous 37 % HCHO and Et3N. All the isolated compounds were spectroscopically characterized and, in some cases, structurally determined by single crystal- X-ray crystallography.

KW - Mass spectroscopy

KW - Phenolic amines

KW - Phenolic ligands

KW - Tripod ligands

KW - X-Ray

UR - http://www.scopus.com/inward/record.url?scp=85189034197&partnerID=8YFLogxK

U2 - 10.1016/j.ica.2024.122027

DO - 10.1016/j.ica.2024.122027

M3 - Article

AN - SCOPUS:85189034197

SN - 0020-1693

VL - 566

JO - Inorganica Chimica Acta

JF - Inorganica Chimica Acta

M1 - 122027

ER -

An efficient method for the construction of phenolic compounds incorporating pendant amine arms

Abstract

Keywords

ASJC Scopus subject areas

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