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Issue 10, 2012
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Switching between ring closed and open N-incorporated heterocycles with tuneable charges and modular reactivity based upon 5-(2-bromoethyl)phenanthridinium bromide

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Abstract

5-(2-bromoethyl)phenanthridinium bromide (BEP) undergoes a 3-step-one-pot cyclisation reaction with primary amines allowing the facile synthesis of a vast library of heterocycles. A diverse range of primary aryl amines were explored as reactants to gain insight into the product isolated as a result of the steric and electronic effects of the aryl precursors. Analysis and reaction monitoring with UV-vis and NMR spectroscopy revealed that excessively electron withdrawing groups and sterically hindered amines do not allow for isolation of the common neutral tetrahydroimidazophenanthridine (TIP) structure but allow either the isolation of the charged dihydroimadazophenanthridinium (DIP) or aminoethylphenanthridinium (AEP) products.

Graphical abstract: Switching between ring closed and open N-incorporated heterocycles with tuneable charges and modular reactivity based upon 5-(2-bromoethyl)phenanthridinium bromide

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Article information


Submitted
09 Oct 2011
Accepted
20 Dec 2011
First published
06 Feb 2012

Org. Biomol. Chem., 2012,10, 2026-2034
Article type
Paper

Switching between ring closed and open N-incorporated heterocycles with tuneable charges and modular reactivity based upon 5-(2-bromoethyl)phenanthridinium bromide

R. Eadie, C. Richmond, S. Moreton and L. Cronin, Org. Biomol. Chem., 2012, 10, 2026
DOI: 10.1039/C2OB06708K

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