title: Synthesis of Branched Tryptamines via the Domino Cloke-Stevens/Grandberg Rearrangement.
abstract: The rearrangement of cyclopropylketone arylhydrazones generated in situ from arylhydrazine hydrochlorides and ketones leads to formation of tryptamine derivatives. The use of (2-arylcyclopropyl)ethanones in the reactions with model 4-bromophenylhydrazine hydrochloride gives branched tryptamines with aryl groups in the α-position to the amino group, while (2-methylcyclopropyl)ethanone gives a mixture of α- and β-substituted products in a ratio of 1:3. The method was found effective in the synthesis of enantiomerically pure tryptamine. Thus, (R,R)-(2-phenylcyclopropyl)ethanone gives the (S)-α-phenyltryptamine derivative with an enantiomeric excess over 99%.
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences , 47 Leninsky prospect, 119991 Moscow, Russian Federation.
authors.forename: Rinat F
authors.initials: RF
authors.lastname: Salikov
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences , 47 Leninsky prospect, 119991 Moscow, Russian Federation.|Higher Chemical College, Russian Academy of Sciences , 125047 Moscow, Russian Federation.
authors.forename: Konstantin P
authors.initials: KP
authors.lastname: Trainov
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences , 47 Leninsky prospect, 119991 Moscow, Russian Federation.|Higher Chemical College, Russian Academy of Sciences , 125047 Moscow, Russian Federation.
authors.forename: Anastasia A
authors.initials: AA
authors.lastname: Levina
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences , 47 Leninsky prospect, 119991 Moscow, Russian Federation.|Moscow Chemical Lyceum , 4 Tamozhennyj Proezd, 111033 Moscow, Russian Federation.
authors.forename: Irina K
authors.initials: IK
authors.lastname: Belousova
authors.affiliation: A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences , 119991 Moscow, Russian Federation.
authors.forename: Michael G
authors.initials: MG
authors.lastname: Medvedev
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences , 47 Leninsky prospect, 119991 Moscow, Russian Federation.
authors.forename: Yury V
authors.identifier: 0000-0002-3433-7571
authors.initials: YV
authors.lastname: Tomilov