Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, College of Chemistry and Materials Science, Key Laboratory of Chemical Biology of Hebei Province, Hebei University, Baoding, Hebei 071002, PR China.
Jiangsu Collaborative Innovation Center of Chinese Medicinal Resources Industrialization, College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, Jiangsu 210023, PR China.
J Org Chem. 2023 Apr 7;88(7):4854-4862. doi: 10.1021/acs.joc.3c00087. Epub 2023 Mar 22.
A metal/peroxide-free involved simple cascade 6--trig spirocyclization of -butyl nitrite with biaryl ynones has been finished, which resulted in various NO-modified spiro[5,5]trienones with good regioselectivity/yields. A variety of scaled-up experiments, reduction/epoxidation operations, and mechanistic studies were performed to verify the merits and spirocyclization process of this radical system. Finally, the structure of the spirocycles was confirmed by single-crystal X-ray diffraction.
