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; Jos Oomens; Andrea Serraiocco

doi: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

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

^*Autore corrispondente per questo lavoro

Risultato della ricerca: Contributo in rivista › Articolo

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.

Lingua originale	Inglese
pagine (da-a)	1-10
Numero di pagine	10
Rivista	European Journal of Organic Chemistry
Volume	2022
DOI	https://doi.org/10.1002/ejoc.202201166
Stato di pubblicazione	Pubblicato - 2022

Keywords

Carbinols
IRMPD
Indole-2-methides
Nitrogen heterocycles
Synthetic methods

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10.1002/ejoc.202201166

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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. (2022). 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, 1-10. https://doi.org/10.1002/ejoc.202201166

@article{815c7a2033054dadb5cf4ffef8c20388,

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

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.",

keywords = "Carbinols, IRMPD, Indole-2-methides, Nitrogen heterocycles, Synthetic methods, Carbinols, IRMPD, Indole-2-methides, Nitrogen heterocycles, Synthetic methods",

author = "Antonio Arcadi and Giel Berden and Alessia Ciogli and Davide Corinti and Crestoni, \{Maria Elisa\} and \{De Angelis\}, Martina and Giancarlo Fabrizi and Antonella Goggiamani and Antonia Iazzetti and Federico Marrone and Vincenzo Marsicano and Jos Oomens and Andrea Serraiocco",

year = "2022",

doi = "10.1002/ejoc.202201166",

language = "English",

volume = "2022",

pages = "1--10",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

}

Arcadi, A, Berden, G, Ciogli, A, Corinti, D, Crestoni, ME, De Angelis, M, Fabrizi, G, Goggiamani, A, Iazzetti, A, Marrone, F, Marsicano, V, Oomens, J & Serraiocco, A 2022, '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, vol. 2022, pagg. 1-10. https://doi.org/10.1002/ejoc.202201166

TY - JOUR

T1 - Reactivity of Indolylmethylacetates with N, O, and S Soft Nucleophiles: Evidence of 2-Alkylideneindolenines and 3-Alkylideneindoleninium Generation by ESI-MS and IRMPD Spectroscopy

AU - Arcadi, Antonio

AU - Berden, Giel

AU - Ciogli, Alessia

AU - Corinti, Davide

AU - Crestoni, Maria Elisa

AU - De Angelis, Martina

AU - Fabrizi, Giancarlo

AU - Goggiamani, Antonella

AU - Iazzetti, Antonia

AU - Marrone, Federico

AU - Marsicano, Vincenzo

AU - Oomens, Jos

AU - Serraiocco, Andrea

PY - 2022

Y1 - 2022

N2 - 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.

AB - 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.

KW - Carbinols

KW - IRMPD

KW - Indole-2-methides

KW - Nitrogen heterocycles

KW - Synthetic methods

KW - Carbinols

KW - IRMPD

KW - Indole-2-methides

KW - Nitrogen heterocycles

KW - Synthetic methods

UR - http://hdl.handle.net/10807/228416

U2 - 10.1002/ejoc.202201166

DO - 10.1002/ejoc.202201166

M3 - Article

SN - 1434-193X

VL - 2022

SP - 1

EP - 10

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

ER -

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

Abstract

Keywords

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