Reaction of isoquinolines 1 with N-arylsulfonylamino acid fluorides 2 provides a highly stereoselective access to new dihydroimidazo[2,1-a]isoquinolin-3-ones 5 via intermediate N-acylisoquinolinium salts 3. Addition reactions to the enamine double bond, such as hydrogenation or epoxidation with dimethyldioxirane, leads to tetrahydroimidazo[2,1-a]isoquinoline-3-ones 6, 7 and oxiranes 8, respectively. Opening of the oxirane ring of the 8 with nucleophiles allows the synthesis of hydroxytetrahydroimidazo[2,1-a]isoquinolin-3-ones
Key indicatorsSingle-crystal X-ray study T = 180 K Mean '(C±C) = 0.002 A Ê R factor = 0.030 wR factor = 0.082 Data-to-parameter ratio = 13.1 For details of how these key indicators were automatically derived from the article, see
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Fused pyridine derivatives R 0450Asymmetric Synthesis of Isoquinoline Derivatives from Amino Acids. -Reaction of isoquinolines (I) and (XIV) (cf. following scheme) with N-arylsulfonylamino acid fluorides (II) provides a straightforward and highly stereoselective access towards dihydroimidazoisoquinolines. A variety of reactions at the enamine moiety is studied. They involve the double bond hydrogenation, dimerization and highly stereoselective epoxidation reaction. Regiospecific and highly stereoselective oxirane ring opening of the epoxide (VIII) is achieved with diverse nucleophiles like amines, methanol or Tms-O-Tf (to be continued). -(SIECK, O.; EHWALD, M.; LIEBSCHER*, J.; Eur.
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