Year: 2026
Type: article
Abstract: Herein, we report an improved strategy for the synthesis of nitrogen-containing aromatic compounds featuring a nitrogen atom directly attached to a benzene ring. The method relies on a thermal one-pot Diels-Alder/decarboxylation/iodine-catalyzed aromatization cascade reaction starting from 2-pyrones, enabling access to novel C-3-nitrogenated phthalimides and related aromatics in yields of up to 95%. Iodine, a simple and readily available catalyst, was employed to promote the transformation while effectively suppressing the competing second Diels-Alder reaction. Subsequent derivatization demonstrated the synthetic utility of this approach through the preparation of pomalidomide, an immunomodulatory drug.
Source: The Journal of Organic Chemistry
Institution: Universidade Estadual de Campinas (UNICAMP)
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
Awards: EMU: Acquisition of Mass Spectrometers for Integrative Omic Sciences in Environmental Chemistry, Health, Sustainable Chemistry, and Agricultural Technologies, Nuclear magnetic resonance spectroscopy: from pulse sequences to structural assignments, G5051658164, G5815005107, G6262932207, G6438247056, G7115283704, Enabling technologies for the sustainable chemical synthesis of platform molecules, new chemicals and bioactive compounds, EMU scientific: acquisition of a 400 MHz equipment and a 600 MHz console: modernization and expansion of the multi-user NMR center focused on small molecule studies, G941535195
OpenAlex ID: W7147453340