151320-82-0Relevant articles and documents
Regiochemistry of the microwave-assisted reaction between aromatic amines and α-bromoketones to yield substituted 1H-indoles
Vara, Yosu,Aldaba, Eneko,Arrieta, Ana,Pizarro, Jose L.,Arriortua, Maria I.,Cossio, Fernando P.
experimental part, p. 1763 - 1772 (2008/10/09)
The scope and regioselectivity of the Bischler (or Bischler-Moehlau) reaction between aromatic amines and α-bromoketones has been studied by computational and experimental techniques. It has been found that in many cases the reaction yields are improved under microwave irradiation and working in the absence of solvent. When di- and trisubstituted amines are used as substrates the regioselectivity of the reaction is different to that obtained with the corresponding primary anilines. The reaction between benzene-1,2-diamine and α-bromoacetophenones under the same conditions yields 2-substituted quinoxalines instead of indoles. Finally, when pyridin-2-amines and pyrimidine-2-amines are allowed to react with the corresponding α-bromoacetophenones, the corresponding imidazo[1,2-a]pyridines and imidazo[1,2-a]pyrimidines are obtained, respectively. The Royal Society of Chemistry.
Synthesis of Activated 3-Arylindoles
Black, David St. C.,Bowyer, Michael C.,Bowyer, Paul K.,Ivory, Andrew J.,Kim, Mihyong,et al.
, p. 1741 - 1750 (2007/10/02)
A wide range of substituted 3-aryl-4,6-dimethoxyindoles (6) has been synthesized from the related α-anilinoacetophenones (5), in which the nitrogen atom is protected by a trifluoroacetyl or acetyl group.This method has led to the synthesis of a 3,7'-biindolyl (12).