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

Antonio Arcadi,Giel Berden,Alessia Ciogli,Davide Corinti,Maria Elisa Crestoni, Martina De Angelis,Giancarlo Fabrizi,Antonella Goggiamani,Antonia Iazzetti,Federico Marrone,Vincenzo Marsicano, Jo Oomens,Andrea Serraiocco

European Journal of Organic Chemistry（2022）

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摘要

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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关键词

Carbinols,Indole-2-methides,IRMPD,Nitrogen heterocycles,Synthetic methods

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