1429520-73-9Relevant academic research and scientific papers
Synthesis and reactivity of unsymmetrical azomethine imines formed using alkene aminocarbonylation
Gan, Wei,Moon, Patrick J.,Clavette, Christian,Das Neves, Nicolas,Markiewicz, Thomas,Toderian, Amy B.,Beauchemin, Andre M.
, p. 1890 - 1893 (2013)
Complex cyclic azomethine imines possessing a β-aminocarbonyl motif can be accessed readily from simple alkenes and hydrazones. This alkene aminocarbonylation approach allows formation of ketone-derived azomethine imines of unprecedented complexity. Since unsymmetrical hydrazones are used, two stereoisomers are formed: the reactivity of chiral derivatives is explored in both intra- and intermolecular systems.
Synthesis of 3D-Rich Heterocycles: Hexahydropyrazolo[1,5-A]pyridin-2(1H)-ones and Octahydro-2H-2a,2a1-diazacyclopenta[cd]inden-2-ones
Pu?avec Kirar, Eva,Drev, Miha,Mirnik, Jona,Gro?elj, Uro?,Golobi?, Amalija,Dahmann, Georg,Po?gan, Franc,?tefane, Bogdan,Svete, Jurij
, p. 8920 - 8933 (2016/10/14)
Two cyclic azomethine imines, 7-methyl- and 7-phenyl-2-oxo-Δ7-hexahydropyrazolo[1,5-A]pyridin-8-ium-1-ide, were prepared in seven steps from the respective commercially available δ-keto acids. The addition of Grignard reagents followed by N-Alkylation at position 1 afforded the 1,7,7-trisubstituted hexahydropyrazolo[1,5-A]pyridin-2(1H)-ones, whereas 1,3-dipolar cycloadditions of these dipoles to typical acetylenic and olefinic dipolarophiles gave 4a-substituted 2a,2a1-diazacyclopenta[cd]indene derivatives as the first representatives of a novel heterocyclic system. Regio- and stereoselectivity as well as the mechanism of these [3 + 2]-cycloadditions were evaluated using computational and experimental methods. The data obtained were in agreement with the polar concerted cycloaddition mechanism via the energetically favorable syn/endo-transition states.
