Synthesis, characterisation and crystal structure of a novel pyridyl urea macrocycle
Synthesis, characterisation and crystal structure of a novel pyridyl urea macrocycle
A novel pyridyl urea based macrocycle has been synthesised and fully characterised including a single crystal X-ray structure determination. The synthetic approach first involves the reaction of benzyloxycarbonylaminopropyl-3-isocyanate with t-butyl 2-[(2-aminopyridin-3-yl)oxy]acetate resulting in a coupling product. After deprotection of the amine and acid moieties and coupling subsequent coupling in the presence of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), a macrocycle is formed. The structures of the compounds were confirmed by mass spectrometry and NMR spectroscopy. The X-ray crystal structure of the macrocycle reveals as expected a non-binding conformation with an intramolecular hydrogen bond between the urea NH and the pyridyl nitrogen.
753-757
Perveen, Shagufta
55ee743d-9c88-4623-afbe-14d3a38e3c91
Kilburn, Jeremy
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Al-Taweel, Areej M
4eee5a75-f5a7-420e-9888-d8d4e1fc297a
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Perveen, Shagufta
55ee743d-9c88-4623-afbe-14d3a38e3c91
Kilburn, Jeremy
e5474f1d-b4b2-4d72-9712-7b1a6f340898
Al-Taweel, Areej M
4eee5a75-f5a7-420e-9888-d8d4e1fc297a
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Perveen, Shagufta, Kilburn, Jeremy, Al-Taweel, Areej M and Light, Mark
(2016)
Synthesis, characterisation and crystal structure of a novel pyridyl urea macrocycle.
Journal of Chemical Research, 40 (12), .
(doi:10.3184/174751916X14792878808106).
Abstract
A novel pyridyl urea based macrocycle has been synthesised and fully characterised including a single crystal X-ray structure determination. The synthetic approach first involves the reaction of benzyloxycarbonylaminopropyl-3-isocyanate with t-butyl 2-[(2-aminopyridin-3-yl)oxy]acetate resulting in a coupling product. After deprotection of the amine and acid moieties and coupling subsequent coupling in the presence of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), a macrocycle is formed. The structures of the compounds were confirmed by mass spectrometry and NMR spectroscopy. The X-ray crystal structure of the macrocycle reveals as expected a non-binding conformation with an intramolecular hydrogen bond between the urea NH and the pyridyl nitrogen.
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JCR 1604278 Final revision.pdf
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Accepted/In Press date: 1 December 2016
e-pub ahead of print date: 1 December 2016
Organisations:
Faculty of Natural and Environmental Sciences
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Local EPrints ID: 405556
URI: http://eprints.soton.ac.uk/id/eprint/405556
ISSN: 0308-2342
PURE UUID: 18652b29-5e8c-4afa-abbb-002c9dd570c0
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Date deposited: 07 Feb 2017 15:45
Last modified: 16 Mar 2024 03:04
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Author:
Shagufta Perveen
Author:
Jeremy Kilburn
Author:
Areej M Al-Taweel
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