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.
The absoluteconfiguration of cuauhtemone and related compounds
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine
Role of lipid peroxidation in biliary obstruction in the rat
Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea
Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters