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 Lee |
| 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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