1080-83-7Relevant academic research and scientific papers
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.
A versatile linkage strategy for solid-phase synthesis of N,N-dimethyltryptamines and β-carbolines
Wu, Tom Y. H.,Schulte, Peter G.
, p. 4033 - 4035 (2007/10/03)
(matrix presented) Various tryptamines are captured by a vinylsulfonylmethyl polystyrene resin, generating a safety-catch linkage. β-Carbolines can be formed from 4 by a Pictet-Spengler reaction with the introduction of R1. Tryptamine 4 can also be derivatized by acylation or copper-mediated coupling to introduce R2. If X = Br, Suzuki coupling can be used to introduce R3. After derivatization, the indole derivatives are activated with methyl iodide and released under mild basic condition.
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.
