Synthesis of functionalised azepanes and piperidines from bicyclic halogenated aminocyclopropane derivatives
作者： Cheng Chen , Pullaiah Kattanguru , Olesya A. Tomashenko , Rafał Karpowicz , Gabriela Siemiaszko
DOI: 10.1039/C7OB01238A
关键词: Ring (chemistry) 、 Chemistry 、 Heptane 、 Hexane 、 Reductive amination 、 Cleavage (embryo) 、 Organic chemistry 、 Cyclopropane 、 Bicyclic molecule
摘要: 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 dihalocarbene species with N-Boc-2,3-dihydro-1H-pyrroles or -1,2,3,4-tetrahydropyridines. Monochloro substrates synthesised as well, using a chlorine-to-lithium exchange reaction. The behaviour several aldehydes ketones under reductive amination conditions deprotected halogenated secondary cyclopropylamines was investigated, showing that this transformation typically triggers cyclopropane ring cleavage to give access interesting nitrogen-containing ring-expanded products.
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