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. 2013 Jul 11:9:1407-13.
doi: 10.3762/bjoc.9.157. eCollection 2013.

α-Bromodiazoacetamides - a new class of diazo compounds for catalyst-free, ambient temperature intramolecular C-H insertion reactions

Asmund Kaupang  1 , Tore Bonge-Hansen
Affiliations

α-Bromodiazoacetamides - a new class of diazo compounds for catalyst-free, ambient temperature intramolecular C-H insertion reactions

Asmund Kaupang et al. Beilstein J Org Chem. .

Abstract

In this work, we introduce a new class of halodiazocarbonyl compounds, α-halodiazoacetamides, which through a metal-free, ambient-temperature thermolysis perform intramolecular C-H insertions to produce α-halo-β-lactams. When carried out with α-bromodiazoacetamides bearing cyclic side chains, the thermolysis reaction affords bicyclic α-halo-β-lactams, in some cases in excellent yields, depending on the ring size and substitution pattern of the cyclic amide side chains.

Keywords: diazo; halocarbonylcarbene; halogenation; thermolysis; α-halo-β-lactam.

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Figures

Scheme 1
Scheme 1
Preparation of the diazoacetamides.
Scheme 2
Scheme 2
Bromination of the diazoacetamides 3a–f and thermolysis of the α-bromodiazoacetamides 4a–f.
See this image and copyright information in PMC

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