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

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• 作者：Rinat F. Salikov ; Konstantin P. Trainov ; Anastasia A. Levina ; Irina K. Belousova ; Michael G. Medvedev ; Yury V. Tomilov
• 刊名：Journal of Organic Chemistry
• 出版年：2017
• 出版时间：January 6, 2017
• 年：2017
• 卷：82
• 期：1
• 页码：790-795
• 全文大小：332K
• ISSN：1520-6904

文摘

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%.