Synthesis of Branched Tryptamines via the Domino Cloke–Stevens/Grandberg Rearrangement

Synthesis of Branched Tryptamines via the Domino Cloke–Stevens/Grandberg Rearrangement Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2017, Volume: 82, Number: 1, Pages: 790-795 Pages count : 6 DOI: 10.1021/acs.joc.6b02578

Authors

Salikov Rinat F. ¹ , Trainov Konstantin P. ^2,1 , Levina Anastasia A. ^2,1 , Belousova Irina K. ^1,3 , Medvedev Michael G. ⁴ , Tomilov Yury V. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prospect, 119991, Moscow, Russian Federation
2	Higher Chemical College, Russian Academy of Sciences, 125047 Moscow, Russian Federation
3	Moscow Chemical Lyceum, 4 Tamozhennyj Proezd, 111033 Moscow, Russian Federation
4	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991, Moscow, Russian Federation.

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%.

Salikov R.F. , Trainov K.P. , Levina A.A. , Belousova I.K. , Medvedev M.G. , Tomilov Y.V.
Synthesis of Branched Tryptamines via the Domino Cloke–Stevens/Grandberg Rearrangement
Journal of Organic Chemistry. 2017. V.82. N1. P.790-795. DOI: 10.1021/acs.joc.6b02578 WOS Scopus OpenAlex

≡ Web of science:	WOS:000391781900081
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