Synthesis of N-[(dialkylamino)methyl)]acrylamides and 
N-[(dialkylamino)methyl]methacrylamides from Schiff base salts: useful building blocks for smart polymers

Abdullah Alzahrani; Styliana I. Mirallai; Benjamin A. Chalmers; Patrick McArdle; Fawaz Aldabbagh

doi:10.1039/C8OB00811F

Synthesis of N-[(dialkylamino)methyl)]acrylamides and N-[(dialkylamino)methyl]methacrylamides from Schiff base salts: useful building blocks for smart polymers

Abdullah Alzahrani
, Styliana I. Mirallai
, Benjamin A. Chalmers
, Patrick McArdle
, Fawaz Aldabbagh

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

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Abstract

The traditional thermal Mannich reaction is unsuitable for preparing polymerizable N-methylene amino substituted acrylamides and methacrylamides. Herein we provide a facile multi-gram high yield synthesis of these monomeric precursors to stimuli-responsive polymers by addition of acrylamide and methacrylamide onto in situ generated or freshly isolated methylene Schiff base (iminium) salts. X-ray crystal structure of the hydrated iminium salt, 1-(hydroxymethyl)azocan-1-ium chloride and monomer.HCl salt, (N-[(azocan-1-yl)methyl]prop-2-enamide hydrochloride) is described.

Original language	English
Pages (from-to)	4108-4116
Journal	Organic and Biomolecular Chemistry
Volume	22
Early online date	9 May 2018
DOIs	https://doi.org/10.1039/C8OB00811F
Publication status	Published - 14 Jun 2018

Bibliographical note

Note: This work was supported by Ministry of Education of the Kingdom of Saudi Arabia and the Irish Research Council.

Keywords

Chemistry

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10.1039/C8OB00811FLicence: CC BY-NC

Aldabbagh-F-41156-VoR-1Final published version, 754 KBLicence: CC BY-NC

Cite this

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title = "Synthesis of N-[(dialkylamino)methyl)]acrylamides and N-[(dialkylamino)methyl]methacrylamides from Schiff base salts: useful building blocks for smart polymers",

abstract = "The traditional thermal Mannich reaction is unsuitable for preparing polymerizable N-methylene amino substituted acrylamides and methacrylamides. Herein we provide a facile multi-gram high yield synthesis of these monomeric precursors to stimuli-responsive polymers by addition of acrylamide and methacrylamide onto in situ generated or freshly isolated methylene Schiff base (iminium) salts. X-ray crystal structure of the hydrated iminium salt, 1-(hydroxymethyl)azocan-1-ium chloride and monomer.HCl salt, (N-[(azocan-1-yl)methyl]prop-2-enamide hydrochloride) is described.",

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author = "Abdullah Alzahrani and Mirallai, \{Styliana I.\} and Chalmers, \{Benjamin A.\} and Patrick McArdle and Fawaz Aldabbagh",

note = "Note: This work was supported by Ministry of Education of the Kingdom of Saudi Arabia and the Irish Research Council.",

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doi = "10.1039/C8OB00811F",

language = "English",

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Synthesis of N-[(dialkylamino)methyl)]acrylamides and N-[(dialkylamino)methyl]methacrylamides from Schiff base salts: useful building blocks for smart polymers. / Alzahrani, Abdullah; Mirallai, Styliana I.; Chalmers, Benjamin A. et al.
In: Organic and Biomolecular Chemistry, Vol. 22, 14.06.2018, p. 4108-4116.

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

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T1 - Synthesis of N-[(dialkylamino)methyl)]acrylamides and N-[(dialkylamino)methyl]methacrylamides from Schiff base salts

T2 - useful building blocks for smart polymers

AU - Alzahrani, Abdullah

AU - Mirallai, Styliana I.

AU - Chalmers, Benjamin A.

AU - McArdle, Patrick

AU - Aldabbagh, Fawaz

N1 - Note: This work was supported by Ministry of Education of the Kingdom of Saudi Arabia and the Irish Research Council.

PY - 2018/6/14

Y1 - 2018/6/14

N2 - The traditional thermal Mannich reaction is unsuitable for preparing polymerizable N-methylene amino substituted acrylamides and methacrylamides. Herein we provide a facile multi-gram high yield synthesis of these monomeric precursors to stimuli-responsive polymers by addition of acrylamide and methacrylamide onto in situ generated or freshly isolated methylene Schiff base (iminium) salts. X-ray crystal structure of the hydrated iminium salt, 1-(hydroxymethyl)azocan-1-ium chloride and monomer.HCl salt, (N-[(azocan-1-yl)methyl]prop-2-enamide hydrochloride) is described.

AB - The traditional thermal Mannich reaction is unsuitable for preparing polymerizable N-methylene amino substituted acrylamides and methacrylamides. Herein we provide a facile multi-gram high yield synthesis of these monomeric precursors to stimuli-responsive polymers by addition of acrylamide and methacrylamide onto in situ generated or freshly isolated methylene Schiff base (iminium) salts. X-ray crystal structure of the hydrated iminium salt, 1-(hydroxymethyl)azocan-1-ium chloride and monomer.HCl salt, (N-[(azocan-1-yl)methyl]prop-2-enamide hydrochloride) is described.

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