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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...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
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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. |
format | Online Article Text |
id | pubmed-10053697 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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