Guillaume Poissonnet

Synthesis of β-carboline-benzodiazepine hybrid molecules and their amputated analogues as novel ligands of the benzodiazepine receptor

Abstract Two approaches to the synthesis of substituted β-carboline-benzodiazepine hybrid molecules, novel ligands of the benzodiazepine receptor of the central nervous system, were utilized. The first involved DDQ-promoted dehydrogenation of a tetrahydro-β-carboline-benzodiazepine derivative while the second method made use of a triflic anhydride-activated intramolecular condensation of the carboxylic acid functionality of a C-3 anthranilamide of a β- carboline onto N-2. These two techniques were also applied to the synthesis of “amputated” hybrid derivatives in which important structural features (ring A, ring E, C-1) of these molecules were absent.

Practical Syntheses of 5-Trifluoromethyl-1H-indoles

Short and convenient syntheses of 5-trifluoromethyltryptamine and 5-trifluoromethyltryptophole have been realized via a regioselective, palladium catalyzed, coupling/annulation method involving functionalized alkynes and 2-iodo-4-trifluoromethylaniline. A new and improved approach for the preparation of 5-trifluoromethyl-1 H -indole is also described.

Generation of β-carboline azomethine ylides via trimethylsilylmethyl trifluoromethane sulfonate quaternisations: entry into the new class of 11H-indolizino[8,7-b]indole heterocycles

Abstract Norharman ( 1a ), ethyl N-tosyl-β-carboline-3-carboxylate ( 1b ) and N-benzyl-3,4-dihydronorharman ( 4 ) were quaternised with trimethylsilylmethyl trifluoromethane sulfonate and the corresponding azomethine ylides were generated with caesium fluoride; 1,3-dipolar cycloaddition of these ylides with diethyl acetylene dicarboxylate yielded the first known examples of 11 H -indolizino[8,7- b ]indoles.