pHarmacist
(pHantasticant)
07-03-03 16:32
No 444232
       Nitroethene in DIRECT substitution to Indole  Bookmark   

Wow! Nitroethene is sufficiently electrophilic to substitute indole without the need of acid catalyst, the yield is 80% at room temperature:

[image]

I'll bee back with the detailed experimental procedure...
Accept No Imitations, There Can Only Bee One; www.the-hive.ws 		 
 
 
 
    Rhodium
(Chief Bee)
07-03-03 16:50
No 444239
       Nitroethene & DMANE  Bookmark   

Yup, it is - a lot of Repke's publications use this synthon for making tryptamines. 1-Dimethylamino-2-nitroethene (DMANE) is also pretty good: https://www.rhodium.ws/chemistry/dmane.html 		 
 
 
 
    Vitus_Verdegast
(Hive Bee)
07-06-03 01:18
No 444778
       Tryptamine, synthesis starting with ...  Bookmark   

Tryptamine,  synthesis starting with nitroethylene and indole:  Noland, Hartman, J. Am. Chem. Soc. 76, 3227 (1954)
http://www.poedecoder.com/Qrisse/works/dreamw.html 		 
 
 
 
    Rhodium
(Chief Bee)
07-06-03 02:43
No 444794
       Tryptamine Through Nitroethylation of Indole  Bookmark   

The Nitroethylation of Indole. A New Synthesis of Tryptamine.
Wayland E. Noland, Philip J. Hartman
J. Am. Chem. Soc. 76(12), 3227-3228 (1954) (https://www.rhodium.ws/pdf/tryptamine.indole.nitroethylation.pdf)

Edit: I have backed up the great article from pHarmacist's post below to my page for safekeeping: JOC 45, 1185-1189 (1980) (https://www.rhodium.ws/pdf/nitroethene.in.organic.synthesis.pdf) 		 
 
 
 
    pHarmacist
(pHantasticant)
07-07-03 10:32
No 445159
       Nitroethylene
(Rated as: excellent) 		 Bookmark   

Nitroethylene: A Stable, Clean, and Reactive Agent for Organic Synthesis

J . Org. Chem. 1980,45, 1185-1189
_________
Full-text: http://pharmacist8.tripod.com/jo01295a003.pdf
Accept No Imitations, There Can Only Bee One; www.the-hive.ws