Synthesis of functionalised azepanes and piperidines from bicyclic halogenated aminocyclopropane derivatives

被引：21

作者：

Chen, Cheng ^{[1
]}

Kattanguru, Pullaiah ^{[1
]}

Tomashenko, Olesya A. ^{[1
,2
]}

Karpowicz, Rafal ^{[1
,3
]}

Siemiaszko, Gabriela ^{[1
]}

Bhattacharya, Ahanjit ^{[1
]}

Calasans, Vinicius ^{[1
]}

Six, Yvan ^{[1
]}

机构：

[1] Univ Paris Saclay, LSO, CNRS, UMR 7652,ENSTA,Ecole Polytech, F-91128 Palaiseau, France

[2] St Petersburg State Univ, Inst Chem, 7-9 Univ Skaya Nab, St Petersburg 199034, Russia

[3] Univ Lodz, Dept Organ Chem, Fac Chem, Tamka 12, PL-91403 Lodz, Poland

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 25期

关键词：

UNCONVENTIONAL NUCLEOTIDE ANALOGS; NONREARRANGED MONOTERPENOID UNIT; SIMPLE INDOLE ALKALOIDS; RING-OPENING REACTIONS; GEM-DIHALOCYCLOPROPANES; DICHLOROCARBENE ADDUCT; LYCOPODIUM ALKALOIDS; ORBITAL SYMMETRY; HUPERZIA-SERRATA; EXPANSION;

D O I：

10.1039/c7ob01238a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

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 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.

引用

页码：5364 / 5372

页数：9

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