Issue 15, 2023

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

Abstract

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.

Graphical abstract: 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

Supplementary files

Article information

Article type
Paper
Submitted
27 Feb 2023
Accepted
23 Mar 2023
First published
29 Mar 2023
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2023,13, 10090-10096

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

A. Goggiamani, A. Arcadi, A. Ciogli, M. De Angelis, S. Dessalvi, G. Fabrizi, F. Iavarone, A. Iazzetti, A. Sferrazza and R. Zoppoli, RSC Adv., 2023, 13, 10090 DOI: 10.1039/D3RA01335A

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