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.
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, F. Travagin. - In: CHEMICAL COMMUNICATIONS. - ISSN 1359-7345. - 60:70(2024 Aug 27), pp. 9428-9431. [10.1039/d4cc03596h]
A serendipitous one-pot synthesis of the octahydro-2H-pyrazino[1,2-a]pyrazine core
T. Grell;V. Colombo;
2024
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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