Tandem intramolecular photocycloaddition-retro-Mannich fragmentation as a route to indole and oxindole

Tandem intramolecular photocycloaddition-retro-Mannich fragmentation as a route to indole and oxindole

Irradiation of a tryptamine linked through its side-chain nitrogen to an alkylidene malonate residue results in an intramolecular [2 + 2] cycloaddition to the indole 2,3-double bond. The resultant cyclobutane undergoes spontaneous retro-Mannich fission to produce a spiro[indoline-3,3-pyrrolenine] wi...

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Bibliographic Details
Main Author: Li, Yang
Other Authors: White, James D.
Language:en_US
Published: 2012
Subjects:
Intramolecular Photocycloaddition
retro-Mannich Fragmentation
Indole
Oxindole
Mannich reaction
Ring formation (Chemistry)
Organic photochemistry
Indole > Synthesis
Natural products > Synthesis
Aromatic compounds > Synthesis
Alkaloids > Synthesis
Heterocyclic compounds > Synthesis
Online Access:http://hdl.handle.net/1957/28312

Internet

http://hdl.handle.net/1957/28312

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