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Beilstein J. Org. Chem. 2018, 14, 2923–2930, doi:10.3762/bjoc.14.271
Graphical Abstract
Figure 1: Chemical structures of analogues.
Scheme 1: Strategy for the formation of 1-(arylamino)-1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-diones.
Scheme 2: Synthesis of the starting (L)-α-amino acid phenylhydrazides and 4-chlorophenylhydrazides 3a–m under...
Scheme 3: Cyclocondensation of 2-formylbenzoic acid (4) with (L)-alanine phenylhydrazide (3a).
Scheme 4: Synthesis of the nitrogenated tricyclic compounds 5a–m. Diastereoisomeric (dr) and enantiomeric (er...
Figure 2: NOEs correlation showing the stereochemistry of the compound 5a.
Figure 3: X-ray crystal structure of 5f shown at the 30% probability level.
Scheme 5: Proposed partial mechanism with a selectivity model.