Novel, versatile three-step synthesis of 1,2,3,4,10,10a-hexahydropyrazino[1,2-a]indoles by intramolecular carbene-mediated C-H insertion
Date
2010
Authors
Krogsgaard-Larsen, N.
Begtrup, M.
Herth, M.M.
Kehler, J.
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Synthesis (La Plata), 2010; 2010(24):4287-4299
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Niels Krogsgaard-Larsen, Mikael Begtrup, Matthias M. Herth, Jan Kehler
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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.
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© Georg Thieme Verlag Stuttgart