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https://hdl.handle.net/2440/87840
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Type: | Journal article |
Title: | Novel, versatile three-step synthesis of 1,2,3,4,10,10a-hexahydropyrazino[1,2-a]indoles by intramolecular carbene-mediated C-H insertion |
Author: | Krogsgaard-Larsen, N. Begtrup, M. Herth, M.M. Kehler, J. |
Citation: | Synthesis (La Plata), 2010; 2010(24):4287-4299 |
Publisher: | Thieme |
Issue Date: | 2010 |
ISSN: | 0328-1205 1437-210X |
Statement of Responsibility: | Niels Krogsgaard-Larsen, Mikael Begtrup, Matthias M. Herth, Jan Kehler |
Abstract: | A 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. |
Keywords: | 1,2,3,4,10,10a-hexahydropyrazino[1,2-a]indoles C-H insertion phenylpiperazine carbene cyclization |
Rights: | © Georg Thieme Verlag Stuttgart |
DOI: | 10.1055/s-0030-1258967 |
Published version: | http://dx.doi.org/10.1055/s-0030-1258967 |
Appears in Collections: | Aurora harvest 7 Chemistry and Physics publications |
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