Vj. Demopoulos et al., SYNTHESIS OF ETRAHYDRO-N,N-DI-N-PROPYL-1H-BENZ[G]INDOL-7-AMINE, A POTENTIAL DOPAMINE-RECEPTOR AGONIST, Journal of heterocyclic chemistry, 32(4), 1995, pp. 1145-1148
In this work, the synthesis of tetrahydro-N,N-di-n-propyl-1H-benz[g]in
dol-7-amine (1) is described. This compound was designed as an indole
bioisostere to the known dopamine receptor agonist 5-OH-aminotetraline
2. The key step of the synthesis was a Mukaiyama type aldol condensat
ion between the dimethyl acetal of 1-(p-toluenesulfonyl)pyrrole-3-acet
aldehyde (4) and 4-di-n-propylamino-1-trimethylsilyloxycyclohexene (8)
followed by cycloaromatization to afford tetrahydro-N,N-di-n-propyl-1
H-benz[g]indol-7-amine (10). Scission of the sulfonamide bond in 10 ga
ve the target compound 1. A byproduct which was isolated was assigned
to the structure of fonyl)-6-[3-[1-(p-toluenesulfonyl)]pyrrolyl]indole
(11). This compound was also synthesized in good yield by an acid cat
alyzed dimerization of the dimethyl acetal of 1 -(p-toluenesulfonyl)py
rrole-3-acetaldehyde (4). Preliminary screening of 1 indicated that it
possesses central dopamine receptor agonist properties.