Depending on the nature of the solvent, alcohol or DMF, N-phenylbenzamidine shows different nucleophilic behaviour towards the conjugated azo-ene system of 1,2-diaza-1,3-dienes. In alcohol it reacts as a nucleophile through the N-phenyl imino nitrogen affording spiro pyrroloimidazoles and 1,3-diphenyl-1H-imidazoles. In DMF, by contrast, it behaves as nucleophile mainly by means of the imino amidino nitrogen providing 2-phenylimidazole derivatives by loss of the aniline molecule. (C) 2010 Elsevier Ltd. All rights reserved.
Attanasi, O.A., Bartoccini, S., Giorgi, G., Mantellini, F., Perrulli, F.R., Santeusanio, S. (2010). Study of the nucleophilic behaviour of N-phenylbenzamidine towards 1,2-diaza-1,3-dienes: domino reactions for imidazole scaffolds. TETRAHEDRON, 66(27-28), 5121-5129 [10.1016/j.tet.2010.04.108].
Study of the nucleophilic behaviour of N-phenylbenzamidine towards 1,2-diaza-1,3-dienes: domino reactions for imidazole scaffolds
Giorgi, Gianluca;
2010-01-01
Abstract
Depending on the nature of the solvent, alcohol or DMF, N-phenylbenzamidine shows different nucleophilic behaviour towards the conjugated azo-ene system of 1,2-diaza-1,3-dienes. In alcohol it reacts as a nucleophile through the N-phenyl imino nitrogen affording spiro pyrroloimidazoles and 1,3-diphenyl-1H-imidazoles. In DMF, by contrast, it behaves as nucleophile mainly by means of the imino amidino nitrogen providing 2-phenylimidazole derivatives by loss of the aniline molecule. (C) 2010 Elsevier Ltd. All rights reserved.
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https://hdl.handle.net/11365/10343
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