Synthesis of highly substituted 1,2-diazetidin-3-ones, small ring scaffolds for drug discovery

Santos, Marilla S. and Nortcliffe, Andrew and Lewis, William and Bradshaw, Tracey D and Moody, Christopher J. (2018) Synthesis of highly substituted 1,2-diazetidin-3-ones, small ring scaffolds for drug discovery. Chemistry - a European Journal . ISSN 1521-3765

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Abstract

1,2-Diazetidin-3-ones are readily accessible, small ring scaffolds that upon functionalization have the potential to produce diverse 3-dimensional structures for drug discovery. Thus treatment of diazo hydrazides, obtained from simple hydrazides and malonyl half ester derivatives, followed by diazo transfer, with catalytic amounts of rhodium (II) acetate dimer results in intramolecular carbenoid N–H insertion to give 1,2-diazetidin-3-ones. Although subsequent functionalization reactions could be hampered by the lability of the 4-membered ring, a wide range of new derivatives was available by deprotection at N-1, and subsequent amide or urea formation. The structures of four four-membered rings was confirmed by X-ray crystallography; the compounds showed modest growth inhibitory activity in mammary carcinoma cells.

Item Type: Article
Additional Information: This is the peer reviewed version of the following article: Santos, Marilla S and Nortcliffe, Andrew and Lewis, William and Bradshaw, Tracey D and Moody, Christopher J (2018) Synthesis of highly substituted 1,2-diazetidin-3-ones, small ring scaffolds for drug discovery. Chemistry - a European Journal, doi:10.1002/chem.201801309, which has been published in final form at https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201801309. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: https://doi.org/10.1002/chem.201801309
Depositing User: Smith, Ruth
Date Deposited: 19 Apr 2018 12:03
Last Modified: 31 Mar 2019 04:30
URI: http://eprints.nottingham.ac.uk/id/eprint/51269

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