Synthesis of functionalised azepanes and piperidines from bicyclic halogenated aminocyclopropane derivativesElectronic supplementary information (ESI) available. See DOI: 10.1039/c7ob01238a

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-1 H -pyrroles or -1,2,3,4-tetrahydropyridines. Monochloro substrates were synthesised as well, using a chlorine-to-lithi...

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Main Authors Chen, Cheng, Kattanguru, Pullaiah, Tomashenko, Olesya A, Karpowicz, Rafa, Siemiaszko, Gabriela, Bhattacharya, Ahanjit, Calasans, Vinícius, Six, Yvan
Format Journal Article
LanguageEnglish
Published 27.06.2017
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Summary: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-1 H -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. Reductive amination of aldehydes or ketones with suitable dihalogenated bicyclic aminocyclopropanes gives functionalised ring-expanded products in a single step.
Bibliography:10.1039/c7ob01238a
Electronic supplementary information (ESI) available. See DOI
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob01238a