Dearomatization Reactions of N-OMe Ureas

Authors

• Nazmee Parveen, The University of Texas at Arlington
• Marian N. Aziz, The University of Texas at Arlington
• Delphine Gout, The University of Texas at Arlington
• Carl J. Lovely, Mississippi State University

ORCID

Lovely: https://orcid.org/0000-0001-7012-2001

MSU Affiliation

College of Arts and Sciences; Department of Chemistry

Creation Date

2026-06-30

Abstract

In an attempt to control chemoselectivity in the dearomatization reactions of benzylic ureas, the corresponding N-methoxy ureas were evaluated as stabilized nitrenium ion equivalents. Substrates derived from secondary amines undergo cyclization upon treatment with iodosobenzene diacetate to afford the corresponding spirocyclic ureas in modest to excellent yield. The scope and limitations of this transformation are reported. In addition, some reactions of the dearomatized product are described, resulting in the construction of fragments of the marine alkaloid KB343.

Publication Date

9-25-2025

Publication Title

Organic Letters

Publisher

Oxford University Press [University Publisher]; Entomological Society of America [Society Publisher]

First Page

11307

Last Page

11312

Rights

© 2025 The Authors

Recommended Citation

Parveen, N., Aziz, M. N., Gout, D., & Lovely, C. J. (2025). Dearomatization Reactions of N-OMe Ureas. Organic Letters, 27(40), 11307–11312. https://doi.org/10.1021/acs.orglett.5c03607