Abstract
Stable hemiaminals can be obtained in the one-pot reaction between 2-aminopyrimidine and nitrobenzaldehyde derivatives. Ten new hemiaminals have been obtained, six of them in crystal state. The molecular stability of these intermediates results from the presence of both electron-withdrawing nitro groups as substituents on the phenyl ring and pyrimidine ring, so no further stabilisation by intramolecular interaction is required. Hemiaminal molecules possess a tetrahedral carbon atom constituting a stereogenic centre. As the result of crystallisation in centrosymmetric space groups both enantiomers are present in the crystal structure.
Highlights
Hemiaminals are intermediate products in the process of forming imines from carbonyl compounds and primary amines (Scheme 1)
In our previous papers [19,20] we have reported that the proper choice of reactants concerning their electronic properties can lead to stable hemiaminals
To further investigate the role of the amine moiety on the nature of the obtained products, reactions between 2-aminopyrimidine and benzaldehydes containing electron-withdrawing nitro groups were performed under neutral conditions
Summary
Hemiaminals are intermediate products in the process of forming imines from carbonyl compounds (aldehydes or ketones) and primary amines (Scheme 1). Isolation from the external environment is one of the factors stabilising hemiaminal moieties. Such seclusion can be achieved by means of conducting reactions inside a macromolecular synthetic receptor [2,3,4] or within metal-organic frameworks [5,6]. Reaction scheme between carbonyl compounds and primary amines. The molecular structure of the obtained hemiaminal is stabilised by the resulting intramolecular hydrogen bonding scheme. All the obtained new organic compounds were characterised by elemental analysis, NMR spectroscopy (1H, 13C, HMQC, HMBC), IR spectroscopy, ESI-MS and for crystalline state compounds, single crystal X-ray measurements
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
