Centro de Quı́mica-Fı́sica Molecular (CQFM) and Institute of Nanosciences and Nanotechnology (IN), Departamento de Engenharia Quı́mica e Biológica, Instituto Superior Técnico, 1049-001 Lisboa, Portugal, REQUIMTE, Departamento de Quı́mica, Faculdade de Ciências e Tecnologia da Universidade Nova de Lisboa, Quinta da Torre, 2829-516 Caparica, Portugal, and iMed.UL, Faculdade de Farmácia da Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal

More sustainable approaches for the synthesis of N-based heterocycles.

Simple but efficient: Aza-fused polycyclic quinolines were efficiently assembled through rhodium(III)-based direct double C-H activation of N-aryl azoles followed by cyclization with alkynes without heteroatom-assisted chelation. Copper(II) acetate, aside from acting as an oxidant, could also play an important role in the C-H activation process.

Synthesis of Aza‐Fused Polycyclic Quinolines via Double CH Bond Activation

https://www.rsc.org/suppdata/cc/b5/b501628b/b501628b.pdf

L-Proline promoted Ullmann-type reaction of vinyl bromides with imidazoles in ionic liquids

Highly effective coupling of imidazoles with (E)-vinyl halides can be achieved by using readily available iron catalysts under ligand-free, copper-free and palladium-free conditions. Coupling of (E)-vinyl bromides led to (Z)-products predominantly, while the reactions of (E)-vinyl chlorides afforded (E)-isomers as the major products.

Iron-Catalyzed Cross-Coupling Reaction of Vinyl Bromides or Chlorides with Imidazoles in the Absence of Ligands and Additives

Cu2O-catalyzed Ullmann-type reaction of vinyl bromides with imidazole and benzimidazole

The reaction between the potassium salt of dimethyl imidazole-4,5-dicarboxylate and styrene oxide is shown to produce 4-methoxycarbonyl-1-styrylimidazole-5-carboxylic acid or methyl 5,6-dihydro-8-oxo-6-phenyl-8H-imidazo[5,1-c][1,4]oxazin-1-carboxylate. The subsequent cleavage of this lactone and the use of styrene [18O]oxide indicate the intermediacy of the lactone in the formation of the styryl acid.

Reaction of dimethyl imidazole-4,5-dicarboxylate with styrene oxide

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Reaction of dimethyl imidazole-4,5-dicarboxylate with styrene oxide