[Research on nitrogen heterocyclic compounds. XI. - New synthesis of 3H-benz(e)indole and its derivatives].
Glutaconic esters bearing a 2-naphthylamino moiety and a carbethoxy group at the 4-position underwent thermal decomposition to give 1-carbethoxy-3H-benz[e]indole derivatives. Alkaline hydrolysis of 1-carbethoxy-3H-benz[e]indoles gave the corresponding 3H-benz[e]indoles by loss of the carboxylic group. By this method were synthesized the known 3H-benz[e5indole and the 7-methoxy-3H-benz[e]indole. Glutaconic esters used in this procedure were prepared by condensation of ethyl propiolate with the appropriate 2-naphthylaminomalonate ethyl ester in the presence of a catalytic amount of sodium ethylate.
D002384:Catalysis; D004952:Esters; D006868:Hydrolysis; D007211:Indoles / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D012106:Research; D013055:Spectrophotometry, Infrared
D004952:Esters; D007211:Indoles
Ricerche su composti eterociclici azotati. Nota XI - Una nuova sintesi del 3H-benz[e]indolo e di suoi derivati.