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†,10.1039/D3RA01335A

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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†

Antonella Goggiamani,Antonio Arcadi,Alessia Ciogli,Martina De Angelis,Stefano Dessalvi,Giancarlo Fabrizi,Roberta Zoppoli

RSC Advances Pub Date : 03/29/2023 00:00:00 , DOI:10.1039/D3RA01335A

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.