TY - JOUR

T1 - 5-Diazo Dihydrouracils: Preparation and Some Transformations

AU - Kantin, G.

AU - Sapegin, A.

AU - Dar’in, D.

N1 - Export Date: 27 October 2024 CODEN: JOCEA Сведения о финансировании: Russian Science Foundation, RSF, 22-13-00005 Текст о финансировании 1: This research was supported by the Russian Science Foundation (project grant 22-13-00005). We thank the Research Center for Magnetic Resonance, the Center for Chemical Analysis and Materials Research and the Center for X-ray Diffraction Methods of Saint Petersburg State University Research Park for obtaining the analytical data.

PY - 2024/9/30

Y1 - 2024/9/30

N2 - 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. © 2024 American Chemical Society.

AB - 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. © 2024 American Chemical Society.

KW - Cycloaddition

KW - Scaffolds

KW - 3-dipolar cycloaddition

KW - Carbonyl ylide

KW - Cyclopropanation

KW - Diazo reagents

KW - Dihydrouracil

KW - Dipolar cycloaddition reaction

KW - Heterocycles

KW - Higher yield

KW - Insertion reactions

KW - Modification methods

KW - Reaction intermediates

UR - https://www.mendeley.com/catalogue/06342e29-0688-3cc4-89d8-74c5664dda9f/

U2 - 10.1021/acs.joc.4c01973

DO - 10.1021/acs.joc.4c01973

M3 - статья

VL - 89

SP - 15197

EP - 15205

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 20

ER -