89188-98-7Relevant articles and documents
Single-Pot Synthesis of Alkyl-Substituted Quinolines and Indoles via Photoinduced Oxidation of Primary Alcohols
Makhmutov
, p. 892 - 897 (2018/07/06)
Single-pot synthesis of alkyl-substituted quinolines and indoles has been performed via photoinduced oxidation of primary aliphatic alcohols (C2–C5) and condensation of the aldehydes (products of the alcohols oxidation) with aniline under the action of iron-containing catalysts and inorganic oxidants. The synthesis was the most efficient in the presence of FeCl3·6H2O as catalyst and 10% aqueous solution of NaOCl as oxidant with irradiation by Hg lamp. The synthesis mechanism through photoinduced oxidation of primary aliphatic alcohol has been suggested.
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.
