The cycloaddition reaction of the morpholino enamines of N-methylpiperidone and N-methyl tropinone with sulfonylazides was exploited, leading to a click-chemistry approach to uncommon azacycloalkene monosulfonyl diamines in good yields. A computational model for the key step decomposition of the triazoline intermediate was then realized by DFT calculations. The model explains the observed reaction outcome and leads to a new interpretation of the decomposition mechanism for 5-amino-1,2,3-triazolines.
Click-chemistry approach to azacycloalkene monosulfonyl diamines: synthesis and computational analysis of the reaction mechanism / A. Contini, E. Erba. - In: RSC ADVANCES. - ISSN 2046-2069. - 2:28(2012 Sep), pp. 10652-10660. [10.1039/c2ra21592f]
Click-chemistry approach to azacycloalkene monosulfonyl diamines: synthesis and computational analysis of the reaction mechanism
A. Contini
;E. ErbaUltimo
2012
Abstract
The cycloaddition reaction of the morpholino enamines of N-methylpiperidone and N-methyl tropinone with sulfonylazides was exploited, leading to a click-chemistry approach to uncommon azacycloalkene monosulfonyl diamines in good yields. A computational model for the key step decomposition of the triazoline intermediate was then realized by DFT calculations. The model explains the observed reaction outcome and leads to a new interpretation of the decomposition mechanism for 5-amino-1,2,3-triazolines.File | Dimensione | Formato | |
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