Novel, Versatile Three-Step Synthesis of 1,2,3,4,10,10a-Hexahydropyrazino[1,2-a]indoles by Intramolecular Carbene-Mediated C-H Insertion

作者：Krogsgaard Larsen Niels; Begtrup Mikael; Herth Matthias M; Kehler Jan^*

来源：Synthesis, 2010, (24): 4287-4299.

DOI：10.1055/s-0030-1258967

• 1,2,3,4,10,10a-hexahydropyrazino[1,2-a]indoles
• C-H insertion
• phenylpiperazine
• carbene
• cyclization

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.

• 出版日期2010-12