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

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

SUBMITTER: Kaupang A

PROVIDER: S-EPMC3740503 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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

Kaupang Asmund A Bonge-Hansen Tore T

Beilstein journal of organic chemistry 20130711

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. ...[more]

PMID: 23946835

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