The synthesis of (aminomethyl), (tosylmethyl), and (aryloxymethyl) indoles starting from indolylmethylacetates and N, O, and S soft nucleophiles has been developed. ESI-MS and IR multiple-photon dissociation (IRMPD) spectroscopy analyses confirm the reaction proceeds through a conjugate addition of the nucleophile to 2-alkylideneindolenines and 3-alkylideneindoleninium.
Arcadi, A., Berden, G., Ciogli, A., Corinti, D., Crestoni, M., De Angelis, M., Fabrizi, G., Goggiamani, A., Iazzetti, A., Marrone, F., Marsicano, V., Oomens, J., Serraiocco, A., Reactivity of Indolylmethylacetates with N, O, and S Soft Nucleophiles: Evidence of 2-Alkylideneindolenines and 3-Alkylideneindoleninium Generation by ESI-MS and IRMPD Spectroscopy, <<EUROPEAN JOURNAL OF ORGANIC CHEMISTRY>>, 2022; 2022 (43): 1-10. [doi:10.1002/ejoc.202201166] [https://hdl.handle.net/10807/228416]
Reactivity of Indolylmethylacetates with N, O, and S Soft Nucleophiles: Evidence of 2-Alkylideneindolenines and 3-Alkylideneindoleninium Generation by ESI-MS and IRMPD Spectroscopy
Iazzetti, Antonia
;
2022
Abstract
The synthesis of (aminomethyl), (tosylmethyl), and (aryloxymethyl) indoles starting from indolylmethylacetates and N, O, and S soft nucleophiles has been developed. ESI-MS and IR multiple-photon dissociation (IRMPD) spectroscopy analyses confirm the reaction proceeds through a conjugate addition of the nucleophile to 2-alkylideneindolenines and 3-alkylideneindoleninium.
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