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Synthesis of functionalised azepanes and piperidines from bicyclic halogenated aminocyclopropane derivatives

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Abstract

A series of 6,6-dihalo-2-azabicyclo[3.1.0]hexane and 7,7-dihalo-2-azabicyclo[4.1.0]heptane compounds were prepared by the reaction of dihalocarbene species with N-Boc-2,3-dihydro-1H-pyrroles or -1,2,3,4-tetrahydropyridines. Monochloro substrates were synthesised as well, using a chlorine-to-lithium exchange reaction. The behaviour of several aldehydes and ketones under reductive amination conditions with deprotected halogenated secondary cyclopropylamines was investigated, showing that this transformation typically triggers cyclopropane ring cleavage to give access to interesting nitrogen-containing ring-expanded products.

Graphical abstract: Synthesis of functionalised azepanes and piperidines from bicyclic halogenated aminocyclopropane derivatives

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Publication details

The article was received on 19 May 2017, accepted on 06 Jun 2017 and first published on 06 Jun 2017


Article type: Paper
DOI: 10.1039/C7OB01238A
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Synthesis of functionalised azepanes and piperidines from bicyclic halogenated aminocyclopropane derivatives

    C. Chen, P. Kattanguru, O. A. Tomashenko, R. Karpowicz, G. Siemiaszko, A. Bhattacharya, V. Calasans and Y. Six, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01238A

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