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

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

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2024-08, Vol.60 (70), p.9428-9431
Hauptverfasser: Maestri, Claudio, Minazzi, Paolo, Grell, Toni, Colombo, Valentina, Lattuada, Luciano, Giovenzana, Giovanni B, Travagin, Fabio
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Sprache:eng
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Zusammenfassung:An unexpected nitro group displacement during a nitro-Mannich reaction led to the one-pot formation of the octahydro-2 -pyrazino[1,2- ]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.
ISSN:1359-7345
1364-548X
DOI:10.1039/D4CC03596H