Merck, 357839-5G, 1,5,6,7-Tetrahydro-4H-indol-4-one

General description
Iodination of 1,5,6,7-tetrahydro-4H-indol-4-one using 1-chloromethyl­-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetra­fluoroborate) yields α-iodo derivative as the main product.
Application
Reactant in synthesis of psammopemmin A as antitumor agent
Reactant in synthesis of a 1,3,4,5-tetrahydrobenzindole β-ketoesters and tricyclic tetrahydrobenzindoles via C-H insertion reactions
Reactant in preparation of tricyclic indole and dihydroindole derivatives as inhibitors of guanylate cyclase
Reactant in preparation of condensed pyrroloindoles via Pd-catalyzed intramolecular C-H bond functionalization of (halobenzyl)pyrroles
Reactant in enantioselective preparation of arylalkenyl indoles via asymmetric C-H insertion of rhodium carbenoids followed by Cope rearrangement-elimination

1,5,6,7-Tetrahydro-4H-indol-4-one may be used in the preparation of:
4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carbonitrile
methyl 2-(4-oxo-4,5,6,7-tetrahydro-1H-indol-1-yl)acrylate
3-(4-oxo-4,5,6,7-tetrahydro-1H-indol-1-yl)propanenitrile
potent and orally active 5-HT1A agonists, (R)-(+)- and (S)-(-)-1-formyl-6,7,8,9-tetrahydro-N,N-dipropyl-3H-benz[e]indol-8-amines