1080-83-7Relevant articles and documents
A new synthesis of versatile indolyl-3-carbonylnitriles
Veale, Clinton G.L.
, p. 5287 - 5290 (2015)
Abstract Indolyl-3-carbonylnitriles are compounds with demonstrated utility as intermediates in organic chemistry. However, their synthesis remains a challenge, requiring the use of toxic sources of cyanide, and often proceeding in low yields. Accordingly, presented here is a new synthesis of these versatile reactants, via dehydration of easily accessible α-oxoacetamides in generally high yields under simple reaction conditions.
Intermolecular trapping by indole of a spiroindolenine intermediate formed during the Bischler-Napieralski cyclisation of N-acetyltryptamine
Frost, Jonathan R.,Gaudilliere, Bernard R.P.,Kauffmann, Elisabeth,Loyaux, Denis,Normand, Nadine,Petry, Genevieve,Poirier, Philippe,Wenkert, Ernest,Wick, Alexander E.
, p. 175 - 182 (2007/10/02)
The Bischler-Napieralski cyclisation of N-acetyltryptamine (1a) in the presence of indole (15) affords a moderate yield of the diastereomeric spiroindolines 9 and 10 suggesting the intermediacy of a spiroindolenine 2a in this reaction. Evidence is provided to show that the minor reaction products 2-methyltryptamine (11), tris-(3-indolyl)methane (12) and 6-[(o-aminophenyl) methyl]-5,11-dihydroindolo[3,2-b]carbazole (13) are derived from the spiroindolines 9 and 10.