1173191-69-9Relevant academic research and scientific papers
Synthesis of 5-methylidenehexahydropyrrolo[l,2-a]imidazoles and 6-methylideneoctahydropyrrolo[l,2-a]pyrimidines by the reaction of 1-alkynyl-1-chlorocyclopropanes with lithium derivatives of 1,2- and 1,3-diaminoalkanes
Shavrin,Gvozdev,Nefedov
experimental part, p. 1451 - 1458 (2011/04/16)
A reaction of 1-alkynyl-1-chlorocyclopropanes with excess of lithium derivative of 1,2-diaminoethane leads to 5-methylidenehexahydropyrrolo[l,2-a] imidazoles in 35-72% yields, whereas analogous reaction with lithium derivative of 1,3-diaminopropane gives 6-methyl-ideneoctahydropyrrolo[l,2-a]pyrimidine in up to 50% yield. A mechanism of these unusual multi-step processes includes dehydrochlorination of 1-alkynyl-1-chlorocyclopropanes to form conjugated alkynylcyclopropenes capable of addition of monoalkylamide ions at the double bond, leading to the corresponding secondary cyclopropylamines; the latter under the reaction conditions isomerize to the linear imines, which further undergo a cascade cyclization with sequential involvement of the C=N and C≡C bonds.
5-Methylenehexahydropyrrolo[1,2-a]imidazoles and 6-methyleneoctahydropyrrolo[1,2-a]pyrimidines in the reactions of 1-(alk-1-ynyl)-1-chlorocyclopropanes with lithium derivatives of 1,2- and 1,3-diaminoalkanes
Shavrin, Konstantin N.,Gvozdev, Valentin D.,Nefedov, Oleg M.
scheme or table, p. 300 - 301 (2009/05/27)
Unusual reactions of 1-(alk-1-ynyl)-1-chlorocyclopropanes with lithium derivatives of 1,2-diaminoethane, 1,3-diaminopropane and 1-methylamino-3-aminopropane in THF at 20 °C give previously unknown 5-methylenehexahydropyrrolo[1,2-a]imidazoles and 6-methyleneoctahydropyrrolo[1,2-a]pyrimidines with up to 60% yields.
