Expedient, one-pot preparation of fused indoles via CAN-catalyzed three-component domino sequences and their transformation into polyheterocyclic compounds containing pyrrolo[1,2-a]azepine fragments.
The CAN-catalyzed three-component between reaction between primary amines, beta-dicarbonyl compounds and naphthoquinones or 2-bromonaphthoquinones afforded, respectively, 5-hydroxybenzo[g]indoles and benzo[f]indole-4,9-diones, the former of which were transformed into tetracyclic azepino[1,2-a]benzo[g]indole systems through a gamma-alkylation/ring-closing metathesis sequence.
Suryavanshi
Padmakar A
PA
Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain.
Sridharan
Vellaisamy
V
Menéndez
J Carlos
JC
D000478:Alkylation; D001381:Azepines / Q000737:chemistry*; D002384:Catalysis; D002563:Cerium / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D007700:Kinetics; D009566:Nitrates / Q000737:chemistry*
D001381:Azepines; D007211:Indoles; D009566:Nitrates; C532772:cerium(IV) ammonium nitrate; D002563:Cerium