A selective synthesis of enamines versus aziridines |
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| Authors: | Dalila Belei Elena Bicu Peter G Jones M Lucian Birsa |
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| Institution: | 1. Department of Organic Chemistry, ‘Al. I. Cuza’ University of Iasi, 700506 Iasi, Romania;2. Institute of Inorganic and Analytical Chemistry, Technical University of Braunschweig, Hagenring 30, D‐38106 Braunschweig, Germany |
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| Abstract: | The reaction of 10‐azidoacetyl‐10H‐phenothiazine with olefinic dipolarophiles depends on the reaction temperature. In refluxing toluene, a mixture of enamine and aziridine is formed in 3:1 ratio. The reaction mechanism appears to involve a Michael‐type addition of the nucleophilic N1 azide atom to the olefinic double bond. In chloroform, a cycloaddition reaction takes place with the formation of a 4,5‐dihydro‐1,2,3‐triazole. The heating of dihydrotriazoles in toluene is accompanied by nitrogen elimination leading to a mixture of enamine and aziridine in 1:3 ratio. J. Heterocyclic Chem., 2011. |
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