Fine Tuning Reactivity: Synthesis and Isolation of 1,2,3,12b-Tetrahydroimidazo[1,2-f]phenanthridines

Richmond, C. J., Eadie, R. M., Parenty, A. D. C. and Cronin, L. (2009) Fine Tuning Reactivity: Synthesis and Isolation of 1,2,3,12b-Tetrahydroimidazo[1,2-f]phenanthridines. Journal of Organic Chemistry, 74(21), pp. 8196-8202. (doi:10.1021/jo901622e)

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Abstract

A facile route for the synthesis and isolation of 1,2,3,12b-tetrahydroimidazo[1,2-f]phenanthridines (TIPs) hits been developed. The heterocycle is a reactive intermediate in the three-step cascade synthesis of 2,3-dihydro-1H-imidazo[1,2-f]phenanthridinium cations (DIPs), a biologically active DNA intercalating framework; however, the intermediate has previously only been characterized in situ Derivatization Of the Structure at the imidazo-N position controls the reactivity of the intermediate with respect to electronic potential and pK(a) allowing isolation of a selection of TIP structures. Correlations between these parameters and reaction outcome have been made, and other influences such its steric and solvent effects have also been investigated.

Item Type:Articles
Keywords:ALKALOIDS CYCLIZATION DIHYDROIMIDAZOPHENANTHRIDINIUM DNA DNA-BINDING AGENTS HYDROGENATION IN-SITU JADOMYCIN-B NK109 ONE-POT PH REACTIVITY REDUCTION
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Parenty, Mr Alexis and Richmond, Mr Craig and Cronin, Professor Leroy
Authors: Richmond, C. J., Eadie, R. M., Parenty, A. D. C., and Cronin, L.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
ISSN:0022-3263

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
461871Evolvable Process Design.Leroy CroninEngineering & Physical Sciences Research Council (EPSRC)EP/F016360/1Chemistry