Reactivity of Indolylmethylacetates with N, O, and S Soft Nucleophiles: Evidence of 2-Alkylideneindolenines and 3-Alkylideneindoleninium Generation by ESI-MS and IRMPD Spectroscopy

Authors :: Arcadi, A
Berden, G
Ciogli, A
Corinti, D
Crestoni, Me
De Angelis, M
Fabrizi, G
Goggiamani, A
Iazzetti, Antonia
Marrone, F
Marsicano, V
Oomens, J
Serraiocco, A
Iazzetti, A (ORCID:0000-0002-7792-774X)
Arcadi, A
Berden, G
Ciogli, A
Corinti, D
Crestoni, Me
De Angelis, M
Fabrizi, G
Goggiamani, A
Iazzetti, Antonia
Marrone, F
Marsicano, V
Oomens, J
Serraiocco, A
Iazzetti, A (ORCID:0000-0002-7792-774X)
Publication Year :: 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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