203245-04-9Relevant academic research and scientific papers
Preparation of N-heterocycles by radical cyclisation of enamides mediated by manganese(III) or copper(I). A comparison of cyclisation methods
Davies, David T.,Kapur, Neha,Parsons, Andrew F.
, p. 3941 - 3949 (2007/10/03)
Reaction of enamides with manganese(III) acetate or copper(I) chloride/bipyridine has been investigated. In both cases, an initial 5-endo- trig radical cyclisation reaction took place to produce functionalised pyrrolidinones. The copper(I)-mediated cyclisations were very efficient and bicyclic dienes could be isolated in >80% yield, while the corresponding manganese(III) reactions were generally more problematic, giving related dienes in lower yield (35-52%). (C) 2000 Elsevier Science Ltd.
β- and γ-lactams by nickel powder mediated 4-exo or 5-endo radical cyclisations. A concise construction of the mesembrine skeleton
Cassayre, Jerome,Quiclet-Sire, Beatrice,Saunier, Jean-Baptiste,Zard, Samir Z.
, p. 1029 - 1040 (2007/10/03)
N-Alkenyl trichloroacetamides, upon treatment with nickel powder and acetic acid in refluxing 2-propanol undergo reversible 4-exo radical cyclisation. The cyclised radical can be trapped in different ways leading to β-lactams. When the trap is omitted or not efficient enough, unusual irreversible 5-endo cyclisation occurs affording functionalised five-membered lactams. Synthesis of bicyclic γ-lactams has also been examined providing in few steps an access to the Sceletium alkaloids skeleton.
