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.
Reactivity of Indolylmethylacetates with N, O, and S Soft Nucleophiles: Evidence of 2-Alkylideneindolenines and 3-Alkylideneindoleninium Generation by ESI-MS and IRMPD Spectroscopy / Arcadi, A.; Berden, G.; Ciogli, A.; Corinti, D.; Crestoni, M. E.; De Angelis, M.; Fabrizi, G.; Goggiamani, A.; Iazzetti, A.; Marrone, F.; Marsicano, V.; Oomens, J.; Serraiocco, A.. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1099-0690. - 2022:43(2022), pp. 1-10. [10.1002/ejoc.202201166]
Reactivity of Indolylmethylacetates with N, O, and S Soft Nucleophiles: Evidence of 2-Alkylideneindolenines and 3-Alkylideneindoleninium Generation by ESI-MS and IRMPD Spectroscopy
Ciogli A.;Corinti D.;Crestoni M. E.;De Angelis M.;Fabrizi G.;Goggiamani A.;Iazzetti A.;Marrone F.;Serraiocco A.
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.| File | Dimensione | Formato | |
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