Construction of N‐Heterocycles through Cyclization of Tertiary Amines

Abstract

N‐Heterocycles have been found in a large number of natural products, drug molecules, and bioactive compounds, and they thereby play a vital role in diverse research disciplines including drug discovery, organic synthesis, chemical biology, and material science. To this end, the development of new methods and strategies for the construction of N‐heterocyclic frameworks is arguably one of the most dynamic and significant research areas in organic synthesis. One of these powerful approaches to the synthesis of N‐heterocycles is to establish cyclization reactions based on the transformation of tertiary amines, which has emerged as an attractive research topic. In this Minireview, the significant achievements in the construction of N‐heterocycles through cyclization of tertiary amines are highlighted and a comprehensive overview of the rational design, development, and application of these synthetic methods is presented.

Laccase-Catalyzed 1,4-Dioxane-Mediated Synthesis of Belladine N-Oxides with Anti-Influenza A Virus Activity

“…Amine N -oxides are widely diffused in nature [ 12 , 13 ], and they play an important role as chiral ligands, organo-catalysts, and synthons [ 14 , 15 ]. These compounds are synthetized using hazardous stoichiometric oxidants, or in the alternative, heavy metal catalysts and hydrogen peroxide (H 2 O 2 ), which leads to the formation of toxic wastes and undesired by-products [ 16 ].…”

Decarboxylative tandem C-N coupling with nitroarenes via SH2 mechanism

“…Aromatic tertiary amines, especially bearing benzylic units, are versatile building blocks in organic synthesis, as they contain differentiable C(sp 3 )-H, C-N bond, and C(sp 2 )-H bonds 1 . The biological activity of aromatic tertiary amines and their ability to influence natural neurotransmitter transmission routes enable them highly effective for drug discovery, in areas that range from the treatment of bone deterioration (such as a fracture) 2 to cytopathy (such as cancer) 3 (Fig.…”

Efficient N-arylation of 4-chloroquinazolines en route to novel 4-anilinoquinazolines as potential anticancer agents

“…N-Heterocyclic compounds are commonly present in pharmaceuticals, bioactive natural products, agrochemicals, and synthetic drugs [1,2]. Quinazoline, a benzo-fused N-heterocyclic framework (benzo-1,3-diazine) with relevant biological activities, is recognized as a privileged scaffold in medicinal chemistry [3,4].…”