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Synthesis of 3-substituted 2,3-dihydropyrazino[1,2-a]indol-4(1H)-ones by sequential reactions of 2-indolylmethyl acetates with α-amino acids

The synthesis of 2,3-dihydropyrazino[1,2-a]indol-4(1H)-ones from the sequential reaction of amino acid methyl esters with readily available indole-2-ylmethyl acetates is described. The reaction proceeds in situ under basic conditions of highly unstable and reactive 2-alkylideneindolenines followed b...

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Autores principales: Goggiamani, Antonella, Arcadi, Antonio, Ciogli, Alessia, De Angelis, Martina, Dessalvi, Stefano, Fabrizi, Giancarlo, Iavarone, Federica, Iazzetti, Antonia, Sferrazza, Alessio, Zoppoli, Roberta
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10053697/
https://www.ncbi.nlm.nih.gov/pubmed/37006346
http://dx.doi.org/10.1039/d3ra01335a
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author Goggiamani, Antonella
Arcadi, Antonio
Ciogli, Alessia
De Angelis, Martina
Dessalvi, Stefano
Fabrizi, Giancarlo
Iavarone, Federica
Iazzetti, Antonia
Sferrazza, Alessio
Zoppoli, Roberta
author_facet Goggiamani, Antonella
Arcadi, Antonio
Ciogli, Alessia
De Angelis, Martina
Dessalvi, Stefano
Fabrizi, Giancarlo
Iavarone, Federica
Iazzetti, Antonia
Sferrazza, Alessio
Zoppoli, Roberta
author_sort Goggiamani, Antonella
collection PubMed
description The synthesis of 2,3-dihydropyrazino[1,2-a]indol-4(1H)-ones from the sequential reaction of amino acid methyl esters with readily available indole-2-ylmethyl acetates is described. The reaction proceeds in situ under basic conditions of highly unstable and reactive 2-alkylideneindolenines followed by Michael-type addition of α-amino acid methyl esters/intramolecular cyclization.
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spelling pubmed-100536972023-03-30 Synthesis of 3-substituted 2,3-dihydropyrazino[1,2-a]indol-4(1H)-ones by sequential reactions of 2-indolylmethyl acetates with α-amino acids Goggiamani, Antonella Arcadi, Antonio Ciogli, Alessia De Angelis, Martina Dessalvi, Stefano Fabrizi, Giancarlo Iavarone, Federica Iazzetti, Antonia Sferrazza, Alessio Zoppoli, Roberta RSC Adv Chemistry The synthesis of 2,3-dihydropyrazino[1,2-a]indol-4(1H)-ones from the sequential reaction of amino acid methyl esters with readily available indole-2-ylmethyl acetates is described. The reaction proceeds in situ under basic conditions of highly unstable and reactive 2-alkylideneindolenines followed by Michael-type addition of α-amino acid methyl esters/intramolecular cyclization. The Royal Society of Chemistry 2023-03-29 /pmc/articles/PMC10053697/ /pubmed/37006346 http://dx.doi.org/10.1039/d3ra01335a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Goggiamani, Antonella
Arcadi, Antonio
Ciogli, Alessia
De Angelis, Martina
Dessalvi, Stefano
Fabrizi, Giancarlo
Iavarone, Federica
Iazzetti, Antonia
Sferrazza, Alessio
Zoppoli, Roberta
Synthesis of 3-substituted 2,3-dihydropyrazino[1,2-a]indol-4(1H)-ones by sequential reactions of 2-indolylmethyl acetates with α-amino acids
title Synthesis of 3-substituted 2,3-dihydropyrazino[1,2-a]indol-4(1H)-ones by sequential reactions of 2-indolylmethyl acetates with α-amino acids
title_full Synthesis of 3-substituted 2,3-dihydropyrazino[1,2-a]indol-4(1H)-ones by sequential reactions of 2-indolylmethyl acetates with α-amino acids
title_fullStr Synthesis of 3-substituted 2,3-dihydropyrazino[1,2-a]indol-4(1H)-ones by sequential reactions of 2-indolylmethyl acetates with α-amino acids
title_full_unstemmed Synthesis of 3-substituted 2,3-dihydropyrazino[1,2-a]indol-4(1H)-ones by sequential reactions of 2-indolylmethyl acetates with α-amino acids
title_short Synthesis of 3-substituted 2,3-dihydropyrazino[1,2-a]indol-4(1H)-ones by sequential reactions of 2-indolylmethyl acetates with α-amino acids
title_sort synthesis of 3-substituted 2,3-dihydropyrazino[1,2-a]indol-4(1h)-ones by sequential reactions of 2-indolylmethyl acetates with α-amino acids
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10053697/
https://www.ncbi.nlm.nih.gov/pubmed/37006346
http://dx.doi.org/10.1039/d3ra01335a
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