5-Diazo Dihydrouracils: Preparation and Some Transformations.

Autor: Kantin G; Saint Petersburg State University, Saint Petersburg 199034, Russian Federation., Sapegin A; Saint Petersburg State University, Saint Petersburg 199034, Russian Federation., Dar'in D; Saint Petersburg State University, Saint Petersburg 199034, Russian Federation.; Saint Petersburg Research Institute of Phthisiopulmonology, Saint Petersburg 191036, Russian Federation.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2024 Oct 18; Vol. 89 (20), pp. 15197-15205. Date of Electronic Publication: 2024 Sep 29.
DOI: 10.1021/acs.joc.4c01973
Abstrakt: An approach to a new type of diazo reagents─diazo dihydrouracils─has been developed, and various transformations of the obtained diazo heterocycles have been studied, demonstrating their high synthetic potential for obtaining structurally diverse derivatives based on the privileged dihydrouracil scaffold. The X-H insertion reactions provide high yields of a variety of 5-substituted dihydrouracils. Cyclopropanation and 1,3-dipolar cycloaddition reactions involving a carbonyl ylide intermediate have been carried out to give spiro-annulated derivatives. The limitations of the modification methods with respect to the nature of substituents on the nitrogen atoms of the diazo heterocycle have been outlined.
Databáze: MEDLINE