A serendipitous one-pot synthesis of the octahydro-2H-pyrazino[1,2-a]pyrazine core

Claudio Maestri; Paolo Minazzi; Toni Grell; Valentina Colombo; Luciano Lattuada; Giovanni B. Giovenzana; Fabio Travagin

doi:10.1039/D4CC03596H

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A serendipitous one-pot synthesis of the octahydro-2H-pyrazino[1,2-a]pyrazine core†

Claudio Maestri,

^ab Paolo Minazzi,^c Toni Grell,

^d Valentina Colombo,

^d Luciano Lattuada,

^e Giovanni B. Giovenzana

^ac and Fabio Travagin

*^a

Author affiliations

* Corresponding authors

^a Dipartimento di Scienze del Farmaco (DSF), Università del Piemonte Orientale, Largo Donegani 2, I-28100 Novara, Italy
E-mail: fabio.travagin@uniupo.it, claudio.maestri@uniupo.it

^b PRC Ticinum Lab srl, Via Bovio 6, 28100 Novara, NO, Italy

^c CAGE Chemicals srl, Via Bovio 6, 28100 Novara, NO, Italy

^d Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy

^e Bracco Imaging SpA, Via Egidio Folli 50, 20134 Milano, Italy

Abstract

An unexpected nitro group displacement during a nitro-Mannich reaction led to the one-pot formation of the octahydro-2H-pyrazino[1,2-a]pyrazine core, representing the shortest access to date to this pharmacologically relevant heterobicyclic system. A mechanistic hypothesis is suggested and supported by specific experiments and HRMS analysis of reaction mixtures.

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DOI: https://doi.org/10.1039/D4CC03596H
Article type: Communication
Submitted: 18 Jul 2024
Accepted: 05 Aug 2024
First published: 06 Aug 2024
This article is Open Access

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Chem. Commun., 2024,60, 9428-9431

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A serendipitous one-pot synthesis of the octahydro-2H-pyrazino[1,2-a]pyrazine core

C. Maestri, P. Minazzi, T. Grell, V. Colombo, L. Lattuada, G. B. Giovenzana and F. Travagin, Chem. Commun., 2024, 60, 9428 DOI: 10.1039/D4CC03596H

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Chemical Communications

A serendipitous one-pot synthesis of the octahydro-2H-pyrazino[1,2-a]pyrazine core†

Abstract

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A serendipitous one-pot synthesis of the octahydro-2H-pyrazino[1,2-a]pyrazine core

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