2011
Valois-Escamilla Ismael, Alvarez-Hernandez Alejandro, Rangel-Ramos Luis Felipe, Suárez-Castillo Oscar Rodolfo, Ayala-Mata Francisco, Zepeda-Vallejo Gerardo . Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor. Tetrahedron Letters 2011, 52, 3726-3728. Elsevier, Holanda. ISSN: 0040-4039 doi:10.1016/j.tetlet.2011.05.040
Abstract
The synthesis of 6-bromo-2-arylindoles starting from readily available 2-iodobenzoic acid is presented. Regioselective bromination of the latter was followed by Curtius rearrangement and trapping of the isocyanate with benzyl alcohol led to the benzyl carbamate of 2-iodo-5-bromoaniline. Chemoselective Sonogashira coupling of this compound with arylacetylenes followed by TBAF induced 5-endo-dig cyclization gave the desired bromo indoles. The method allows selective introduction of a bromine atom at the indole C-6 position.
Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine
Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters
Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase
The absoluteconfiguration of cuauhtemone and related compounds
13C NMR and crystallographic evidence of push-pull effects in furoindolic ?-enamino esters
First Total Synthesis of ()-Flustraminol B
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling