National Key R&D Program of China, PUMC Youth Fund and the Fundamental Research Funds for the Central Universities, and Major State Basic Innovation Program of the Chinese Academy of Medical Sciences.

O6 -Corona[3]arene[3]tetraazines, a new class of macrocyclic compounds, were synthesized efficiently in a one-pot reaction from the nucleophilic aromatic substitution reaction between 1,4-dihydroxybenzene derivatives and 3,6-dichlorotetrazine in warm acetonitrile. In the crystalline structure, the resulting macrocycles adopt highly symmetric structures of a regular hexagonal cavity with all bridging oxygen atoms and tetrazine rings located on the same plane with phenylene units orthogonally orientated. The constitutional aromatic rings are able to rotate around the macrocyclic annulus, depending on the steric effect of the substituents and temperature, in solution. The electron-deficient nature revealed by cyclic voltammetry, differential pulse voltammetry, and characteristic absorbances at a visible region show the O6 -corona[3]arene[3]tetrazines to be suitable macrocyclic receptors for electron-rich guests.

All new: 3-Nitro-5-guanidino-1,2,4-oxadiazole (NOG) was synthesized from diaminoglycoluril with in situ generated dimethyldioxirane (DMDO). The impact sensitivity of NOG is more than 40 J with a decomposition temperature of 290 °C. Some other energetic derivatives have been prepared and characterized.

O-Corona[3]arene[3]tetrazines with expanded cavities were synthesized by one-pot SAr reaction between 3,6-dichlorotetrazine and aromatic diols. The macrocycle-to-macrocycle transformation involving IEDDA of tetrazine moieties with an enamine followed by denitrogenative aromatization afforded O-corona[3]arene[3]pyridazines. O-Corona[6]arenes adopted coronary conformations yielding hexagonal cavities of varied sizes. While O-corona[3]arene[3]pyridazines complexed both C and C in a virtually nonselective manner, O-corona[3]arene[3]tetrazines behaved as selective receptors to complex C with K values up to (3.98 ± 0.08) × 10 M in toluene.

Novel 1,2,3-triazole-derived diarylpyrimidines were discovered as potent HIV-1 NNRTIs.