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; Federica Iavarone; Antonia Iazzetti; Alessio Sferrazza; Roberta Zoppoli

doi:10.1039/D3RA01335A

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,

*^a Antonio Arcadi,

^b Alessia Ciogli,^a Martina De Angelis,^a Stefano Dessalvi,^a Giancarlo Fabrizi,^a Federica Iavarone,^cd Antonia Iazzetti,

^cd Alessio Sferrazza*^ae and Roberta Zoppoli^a

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* Corresponding authors

^a Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy
E-mail: alessia.ciogli@uniroma1.it, m.deangelis@uniroma1.it, stefano.dessalvi@uniroma1.it, giancarlo.fabrizi@uniroms1.it, antonella.goggiamani@uniroma1.it, a.sferrazza@irbm.com, roberta.zoppoli@uniroma1.it

^b Dipartimento di Dipartimento di Scienze Fisiche e Chimiche, Università degli Studi di L'Aquila, Via Vetoio, 67100 Coppito (AQ), Italy
E-mail: antonio.arcadi@univaq.it

^c Dipartimento di Scienze Biotecnologiche di base, Cliniche Intensivologiche e Perioperatorie, Università Cattolica del Sacro Cuore, L.go Francesco Vito 1, 00168 Rome, Italy
E-mail: federica.iavarone@unicatt.it, antonia.iazzetti@unicatt.it

^d Policlinico Universitario ‘A. Gemelli’ Foundation-IRCCS, Rome, Italy

^e Alessio Sferrazza is currently a research scientist in IRBM S.p.A., Medicinal Chemistry Department, Pomezia, Roma, Italy

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.

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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†

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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

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