Syntheses of new quinoline‐containing heterocyclic scaffolds using inter‐ and intramolecular Pd‐catalyzed amination

Abstract

A tandem inter-and intramolecular Pd-catalyzed amination protocol was studied on 4-chloro-3-iodoquinoline and 3-chloro-4-iodoquinoline with different aminohetarenes. Applying this method, ten novel quinoline derivatives and eight new heterocyclic ring systems were synthesized.

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

“…Building upon the work by Maes’s group, 213 , 214 Boganyi and Kámán synthesized more complex tetra- and pentacyclic systems ( 292 , Scheme 61 b). 215 A series of 2-aminopyridines and related nucleophiles (e.g., 2-aminoquinolines, 1-aminoisoquinolines) were successfully coupled to 4-chloro-3-iodoquinoline. The quinoline-fused heterocycles were obtained in 30–84% yield in a domino inter- and intramolecular C–N bond-forming process facilitated by a catalyst based on L7 .…”

“…Next, intramolecular arylation was carried out to yield the α-carbolines in 15–99% yield. Building upon the work by Maes’s group, , Boganyi and Kámán synthesized more complex tetra- and pentacyclic systems ( 292 , Scheme b) . A series of 2-aminopyridines and related nucleophiles (e.g., 2-aminoquinolines, 1-aminoisoquinolines) were successfully coupled to 4-chloro-3-iodoquinoline.…”

Metal free direct formation of various substituted pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5-amines and their further functionalization

“…The recent conditions described by Bogányi et al was applied to our substrates. 17 Various aryl halides substituted in para, meta and ortho were successfully introduced in good to excellent yields (Table 4).…”

Isolation, Synthesis, and Biological Activity of Quindoline, a Valuable­ Indoloquinoline Natural Product and Useful Key Intermediate­

“…Next, the Buchwald-Hartwig reaction was put in place, under Pd(OAc) 2 /Xantphos catalysis and microwave irradiation, 74 thus 68 afforded the diarylamine 72 in 70% yield, which was then cyclized under Heck conditions affording quindoline in 61% yield. In contrast to the work of Maes and co-workers, 71 where the bromine atom was attached to the pendant benzene ring, offering two alternative cyclization Their sequence commenced with 2-chloro-3-nitroquinoline (73), which was prepared in three steps from quinoline.…”