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Novel, versatile three-step synthesis of 1,2,3,4,10,10a-hexahydropyrazino[1,2-a]indoles by intramolecular carbene-mediated C-H insertion

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dc.contributor.authorKrogsgaard-Larsen, N.
dc.contributor.authorBegtrup, M.
dc.contributor.authorHerth, M.M.
dc.contributor.authorKehler, J.
dc.date.issued2010
dc.description.abstractA new convenient three-step synthesis of the privileged CNS scaffold 1,2,3,4,10,10a-hexahydropyrazino[1,2-a]indoles has been developed. The method makes use of an intramolecular carbene-mediated C-H insertion in phenylpiperazine-derived tosyl­hydrazones made from 2-fluorobenzaldehydes. Notably, the piperazine can be replaced with other cyclic nitrogen bases and the methodology is successfully extended to pyrrolidine, piperidine, azepane, morpholine, and homopiperazine.
dc.description.statementofresponsibilityNiels Krogsgaard-Larsen, Mikael Begtrup, Matthias M. Herth, Jan Kehler
dc.identifier.citationSynthesis (La Plata), 2010; 2010(24):4287-4299
dc.identifier.doi10.1055/s-0030-1258967
dc.identifier.issn0328-1205
dc.identifier.issn1437-210X
dc.identifier.urihttp://hdl.handle.net/2440/87840
dc.language.isoen
dc.publisherThieme
dc.rights© Georg Thieme Verlag Stuttgart
dc.source.urihttps://doi.org/10.1055/s-0030-1258967
dc.subject1,2,3,4,10,10a-hexahydropyrazino[1,2-a]indoles
dc.subjectC-H insertion
dc.subjectphenylpiperazine
dc.subjectcarbene
dc.subjectcyclization
dc.titleNovel, versatile three-step synthesis of 1,2,3,4,10,10a-hexahydropyrazino[1,2-a]indoles by intramolecular carbene-mediated C-H insertion
dc.typeJournal article
pubs.publication-statusPublished

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