Synthesis Of Nitrogen-containing Molecules Research Articles

Advances in the synthesis of functionalized tetrahydropyridazines from hydrazones.

The tetrahydropyridazine motif is widely present in plenty of natural products and biologically active molecules. Easily prepared from the condensation of carbonyls with hydrazines, hydrazones are versatile synthetic building blocks that are frequently used in organic synthesis. Hydrazones are also utilized in the synthesis of nitrogen-containing molecules, especially nitrogen-containing heterocycles. The presence of the CN-N unit in the product makes hydrazones ideal substrates for the synthesis of tetrahydropyridazine derivatives. Here, in this review, we summarize the recent progress in the construction of variously substituted tetrahydropyridazines from different hydrazone derivatives together with mechanism discussions.

Nitrogen Heterocycle Synthesis through Hydride Abstraction of Acyclic Carbamates and Related Species: Scope, Mechanism, Stereoselectivity, and Product Conformation Studies.

Acyliminium ions and related species are potent electrophiles that can be quite valuable in the synthesis of nitrogen-containing molecules. This manuscript describes a protocol to form these intermediates through hydride abstractions of easily accessible allylic carbamates, amides, and sulfonamides that avoids the reversibility that is possible in classical condensation-based routes. These intermediates are used in the preparation of a range of nitrogen-containing heterocycles, and in many cases high levels of stereocontrol are observed. Specifically areas of investigation include the impact of chemical structure on oxidation efficiency, the geometry of the intermediate iminium ions, the impact of a substrate stereocenter on stereocontrol, and an examination of transition state geometry.

ChemInform Abstract: Application of Organic Azides for the Synthesis of Nitrogen‐Containing Molecules

AbstractReview: ca. 100 refs.