Study of the nucleophilic behaviour of N-phenylbenzamidine towards 1,2-diaza-1,3-dienes: domino reactions for imidazole scaffolds |
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| Authors: | Orazio A. Attanasi Silvia Bartoccini Gianluca Giorgi Fabio Mantellini Francesca R. Perrulli Stefania Santeusanio |
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| Affiliation: | 1. Institute of Organic Chemistry, Università degli Studi di Urbino “Carlo Bo”, Via I Maggetti 24, 61029 Urbino, Italy;2. Department of Chemisrty, Università degli Studi di Siena, Via Aldo Moro, 53100 Siena, Italy |
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| 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. |
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