6533b824fe1ef96bd12812cc

RESEARCH PRODUCT

Synthesis of a Naphtho-pyrido-Annulated Iodonium Salt and Pd-Catalyzed Transformation to 7H-Naphtho[1,8-bc][1,5]naphthyridine

Heiner DetertJulien LetessierMario GeffeDieter Schollmeyer

subject

chemistry.chemical_classificationTransformation (genetics)ChemistryOrganic ChemistryNitroSalt (chemistry)chemistry.chemical_elementIodineMedicinal chemistryCatalysisAminationCatalysisPalladium

description

Nitropyridylnaphthalene is the central intermediate for the synthesis of naphthonaphthyridine and benzo-δ-carboline. Whereas the Cadogan reaction gives the carboline, transformation of the nitro group to iodo followed by oxidation and cyclization results in an iodonium salt. A twofold Pd-catalyzed amination leads to the naphthyridine.

https://doi.org/10.1055/s-0033-1338530