7147-21-9Relevant academic research and scientific papers
Competition between cyclisation and bisimine formation in the reaction of 1,3-diaminopropanes with aromatic aldehydes
Locke, Julie M.,Griffith, Renate,Bailey, Trevor D.,Crumbie, Robyn L.
experimental part, p. 10685 - 10692 (2010/02/28)
Condensation of 1,3-diamines with aldehydes or ketones gives rise to two major products, the hexahydropyrimidine and the bisimine. Experimental studies of the reaction between a range of aromatic aldehydes and 1,3-diaminopropane or 1,3-diamino-2-propanol establish that the hexahydropyrimidine is favoured by the less nucleophilic amine and by the presence of electron withdrawing groups on the aryl ring of the aldehyde. Calculations indicate that the electronic nature of this aryl ring substituent influences both the relative thermodynamic stability of the final products and the reactivity of the aldehyde as an electrophile.
Thermolysis of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in the presence of N-arylmaleimides
Molchanov,Sipkin,Koptelov,Kostikov
, p. 841 - 851 (2007/10/03)
Heating of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in the presence of N-arylmaleimides gives rise to 2,9-diarylperhydropyrazolo[1,2-a]pyrrolo[3,4-c]pyrazole-1,3-diones. It is presumed that thermal cleavage of the C-N bond in the diaziridine fragment of the 6-aryl-1,5-diazabicyclo[3.1.0]hexanes results in formation of labile azomethinimines that react with N-arylmaleimides to afford the products of 1.3-dipolar cycloaddition. The rate of accumulation thereof depends only on the character of substituents in the aromatic ring of the 1,5-diazabicyclo[3.1.0]hexanes and is independent of maleimide. The thermal isomerization of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes without 1,3-dipolarophiles yields the corresponding 2-pyrazolines.
Studies on Thiazolidinones. Part-XIV: Synthesis of 3,3'-Bisthiazolidinones and 2,2-Disubstituted Thiazolidinones from Azomethines
Sahu, J.,Sahu, T. K.,Naik, S. K.,Nayak, A.
, p. 861 - 863 (2007/10/02)
Several new 3,3'-bisthiazolidinones (III) and 2,2-disubstituted thiazolidinones (VIII) have been synthesised by the cycloadditive dehydration of thioglycolic acid to the azomethin derivatives (II) and (VII) prepared from the aliphatic diamines and heterocyclic monoamines respectively.The structure of the compounds have been confirmed from the spectral data and elemental analysis.The fungicidal and bactericidal activities of the compounds have also been evaluated.
