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 a-amino acid methyl esters/intramolecular cyclization.
Goggiamani, A., Arcadi, A., Ciogli, A., De Angelis, M., Dessalvi, S., Fabrizi, G., Iavarone, F., Iazzetti, A., Sferrazza, A., Zoppoli, R., Synthesis of 3-substituted 2,3-dihydropyrazino[1,2- a]indol-4(1H)-ones by sequential reactions of 2- indolylmethyl acetates with a-amino acids, <<RSC ADVANCES>>, 2023; 13 (15): 10090-10096. [doi:10.1039/d3ra01335a] [https://hdl.handle.net/10807/262296]
Synthesis of 3-substituted 2,3-dihydropyrazino[1,2- a]indol-4(1H)-ones by sequential reactions of 2- indolylmethyl acetates with a-amino acids
Goggiamani, Antonella;Iavarone, Federica;Iazzetti, Antonia;
2023
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 a-amino acid methyl esters/intramolecular cyclization.
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