89188-92-1Relevant articles and documents
Regioselective Indolization of Unsymmetrical Phenylhydrazones by Reaction, at Room Temperature, with PCl3
Baccolini, Graziano,Bartoli, Giuseppe,Marotta, Emanuela,Todesco, Paolo E.
, p. 2695 - 2697 (2007/10/02)
Unsymmetrical ketone phenylhydrazones (1) (R1 ae R2) react with PCl3, at room temperature to give predominantly one, (2), of the two possible 2,3-disubstituted indoles in good to excellent overall yield.When the R1 and R2 groups are very different (R1 = Ph or Me; R2 = alkyl or H) the reaction is highly regioselective leading to exclusive or prevalent formation of the corresponding 3-R1 indoles (2), whereas when R1 and R2 are very similar (R1, R2 = alkyl chains) the regioselectivity is decreased and the indole having the shorter chain in the 3-position predominates, but only slightly.Inspection of the results enables the direction of indolization to be predicted and the positions of the substituents in the 2,3-disubstituted indoles to be assigned with certainty, features not inherent in the classical Fischer indolization.