Alkynylation of halo pyrimidines under Pd/C–copper catalysis: regioselective synthesis of 4- and 5-alkynylpyrimidines

Carbon−Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts

“…175 A selective coupling with various alkynes was achieved in the 4-position of 5-bromo-4-chloropyrimidines 125 (Scheme 35). 176 The remaining bromo substituent could be exchanged by a second alkyne within a subsequent Sonogashira coupling. Position 5 was attacked first by Sonogashira reaction of corresponding 4-chloro-5-iodopyrimidines.…”

“…Position 5 was attacked first by Sonogashira reaction of corresponding 4-chloro-5-iodopyrimidines. 176…”

A Pd-catalyzed direct entry to 11-substituted 6H-isoindolo[2,1-a]indol-6-one derivatives as potential anticancer agents

“…However, this reactivity sequence is known to be altered when the halide is attached to an azomethine carbon (e.g. X-C=N-; X = halogen) 19 and our 5 choice of L 1 and L 2 was also changed accordingly (vide infra).…”

“…However, this reactivity sequence is known to be altered when the halide is attached to an azomethine carbon (e.g. X-C]N-; X ¼ halogen) 19 and our choice of L 1 and L 2 was also changed accordingly (vide infra). Herein we report a Pd-mediated one-step synthesis of 11-substituted 6Hisoindolo[2,1-a]indol-6-ones (2 or D) via a sequential Heck reaction of the corresponding dihalo N-allyl substituted Narylbenzamide derivatives (1) (Scheme 1).…”

New Aryl Derivatives of Quinolinedione and Related Heterocyclic Compounds

“…The surge to employ halogenated quinolines as intermediates in metal‐catalyzed C–C bond formation for construction of complex molecules such as natural products, pharmaceuticals, and material science motivated investigating facile reaction protocol for functionalization of structurally related halogenated quinoline‐5,8‐dione . Quinoline‐5,8‐dione is an active component in various antimalaria, antimicrobial, anagelsic, cardiovascular, anticancer, and anti‐inflammatory drugs .…”