Facile access to C -substituted piperazin-2-ones and mianserin derivative enabled by chemoselective carbene insertion and cyclization cascade

The chemoselective N-H insertion of unsymmetrical diamines into carbene is a longstanding challenge. A simple copper-catalyzed strategy for synthesizing -substituted piperazinones is described, employing easily accessible diazo compounds and 1,2-diamines. The reaction proceeded chemo-selective carbe...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2024-05, Vol.60 (44), p.5691-5694
Main Authors: Kumar, Dharmendra, Unnikrishnan, Urmila, Kuram, Malleswara Rao
Format: Article
Language:English
Subjects:
Carbenes
Chemical synthesis
Diamines
Insertion
Substitutes
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Summary:The chemoselective N-H insertion of unsymmetrical diamines into carbene is a longstanding challenge. A simple copper-catalyzed strategy for synthesizing -substituted piperazinones is described, employing easily accessible diazo compounds and 1,2-diamines. The reaction proceeded chemo-selective carbene insertion at the comparatively less nucleophilic amine, followed by instantaneous cyclization. The protocol was further extended to access NH-free piperazinone, and the synthesis of a Mianserin derivative.
ISSN:1359-7345
1364-548X
DOI:10.1039/d4cc00959b