title: A cycloisomerization/Friedel-Crafts alkylation strategy for the synthesis of pyrano[3,4-b]indoles.
abstract: The synthesis of pyrano[3,4-b]indoles is described. The reaction sequence involves Sonogashira coupling of dihydropyran propargyl ether scaffolds with iodoanilines to afford intermediate indoles. Lewis acid-catalyzed ionization of the dihydropyrans, followed by intramolecular C3 alkylation of the indole, provides the title compounds.
authors: Chemistry Department, Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
authors: Matthew R
authors: MR
authors: Medeiros
authors: Scott E
authors: SE
authors: Schaus
authors: John A
authors: JA
authors: Porco
mesh_terms: D000478:Alkylation; D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000737:chemistry*; D007536:Isomerism; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D007211:Indoles