An Efficient Greener Approach for N-acylation of Amines in Water Using Benzotriazole Chemistry

Tarek S. Ibrahim; Israa A. Seliem; Siva S. Panda; Amany M.M. Al-Mahmoudy; Zakaria K.M. Abdel-Samii; Nabil A. Alhakamy; Hani Z. Asfour; Mohamed Elagawany

doi:10.3390/molecules25112501

An Efficient Greener Approach for N-acylation of Amines in Water Using Benzotriazole Chemistry

Tarek S. Ibrahim, Israa A. Seliem, Siva S. Panda, Amany M.M. Al-Mahmoudy, Zakaria K.M. Abdel-Samii, Nabil A. Alhakamy, Hani Z. Asfour, Mohamed Elagawany

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

6 Scopus citations

Abstract

A straightforward, mild and cost-efficient synthesis of various arylamides in water was accomplished using versatile benzotriazole chemistry. Acylation of various amines was achieved in water at room temperature as well as under microwave irradiation. The developed protocol unfolds the synthesis of amino acid aryl amides, drug conjugates and benzimidazoles. The environmentally friendly synthesis, short reaction time, simple workup, high yields, mild conditions and free of racemization are the key advantages of this protocol.

Original language	English (US)
Article number	2501
Journal	Molecules
Volume	25
Issue number	11
DOIs	https://doi.org/10.3390/molecules25112501
State	Published - Jun 1 2020

Keywords

Acylation
Aryl amide
Benzimidazole
Benzotriazole chemistry
Green chemistry
Microwave
One-pot synthesis

ASJC Scopus subject areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

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10.3390/molecules25112501

Cite this

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title = "An Efficient Greener Approach for N-acylation of Amines in Water Using Benzotriazole Chemistry",

abstract = "A straightforward, mild and cost-efficient synthesis of various arylamides in water was accomplished using versatile benzotriazole chemistry. Acylation of various amines was achieved in water at room temperature as well as under microwave irradiation. The developed protocol unfolds the synthesis of amino acid aryl amides, drug conjugates and benzimidazoles. The environmentally friendly synthesis, short reaction time, simple workup, high yields, mild conditions and free of racemization are the key advantages of this protocol.",

keywords = "Acylation, Aryl amide, Benzimidazole, Benzotriazole chemistry, Green chemistry, Microwave, One-pot synthesis",

author = "Ibrahim, {Tarek S.} and Seliem, {Israa A.} and Panda, {Siva S.} and Al-Mahmoudy, {Amany M.M.} and Abdel-Samii, {Zakaria K.M.} and Alhakamy, {Nabil A.} and Asfour, {Hani Z.} and Mohamed Elagawany",

note = "Funding Information: Funding: This project was funded by the Deanship of Scientific Research (DSR), King Abdulaziz University, Jeddah, under grant No.(RG-8-166-41). The authors, therefore, gratefully acknowledge DSR technical and financial support. Funding Information: This project was funded by the Deanship of Scientific Research (DSR), King Abdulaziz University, Jeddah, under grant No.(RG-8-166-41). The authors, therefore, gratefully acknowledge DSR technical and financial support. Publisher Copyright: {\textcopyright} 2020 by the authors.",

year = "2020",

month = jun,

day = "1",

doi = "10.3390/molecules25112501",

language = "English (US)",

volume = "25",

journal = "Molecules",

issn = "1420-3049",

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number = "11",

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TY - JOUR

T1 - An Efficient Greener Approach for N-acylation of Amines in Water Using Benzotriazole Chemistry

AU - Ibrahim, Tarek S.

AU - Seliem, Israa A.

AU - Panda, Siva S.

AU - Al-Mahmoudy, Amany M.M.

AU - Abdel-Samii, Zakaria K.M.

AU - Alhakamy, Nabil A.

AU - Asfour, Hani Z.

AU - Elagawany, Mohamed

N1 - Funding Information: Funding: This project was funded by the Deanship of Scientific Research (DSR), King Abdulaziz University, Jeddah, under grant No.(RG-8-166-41). The authors, therefore, gratefully acknowledge DSR technical and financial support. Funding Information: This project was funded by the Deanship of Scientific Research (DSR), King Abdulaziz University, Jeddah, under grant No.(RG-8-166-41). The authors, therefore, gratefully acknowledge DSR technical and financial support. Publisher Copyright: © 2020 by the authors.

PY - 2020/6/1

Y1 - 2020/6/1

N2 - A straightforward, mild and cost-efficient synthesis of various arylamides in water was accomplished using versatile benzotriazole chemistry. Acylation of various amines was achieved in water at room temperature as well as under microwave irradiation. The developed protocol unfolds the synthesis of amino acid aryl amides, drug conjugates and benzimidazoles. The environmentally friendly synthesis, short reaction time, simple workup, high yields, mild conditions and free of racemization are the key advantages of this protocol.

AB - A straightforward, mild and cost-efficient synthesis of various arylamides in water was accomplished using versatile benzotriazole chemistry. Acylation of various amines was achieved in water at room temperature as well as under microwave irradiation. The developed protocol unfolds the synthesis of amino acid aryl amides, drug conjugates and benzimidazoles. The environmentally friendly synthesis, short reaction time, simple workup, high yields, mild conditions and free of racemization are the key advantages of this protocol.

KW - Acylation

KW - Aryl amide

KW - Benzimidazole

KW - Benzotriazole chemistry

KW - Green chemistry

KW - Microwave

KW - One-pot synthesis

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DO - 10.3390/molecules25112501

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AN - SCOPUS:85085677369

SN - 1420-3049

VL - 25

JO - Molecules

JF - Molecules

IS - 11

M1 - 2501

ER -

An Efficient Greener Approach for N-acylation of Amines in Water Using Benzotriazole Chemistry

Abstract

Keywords

ASJC Scopus subject areas

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