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:

I'll bee back with the detailed experimental procedure...

Accept No Imitations, There Can Only Bee One;
(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: ../rhodium/chemistry /dmane.html
(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)
(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) (../rhodium/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) (../rhodium/pdf /
07-07-03 10:32
No 445159
(Rated as: excellent)

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

J . Org. Chem. 1980,45, 1185-1189

Accept No Imitations, There Can Only Bee One;