Novel 3,4-dihydro-1,4-oxazine (dehydromorpholine) sulfonamides and sulfones conveniently accessed from suitable a-diazoketones via O[sbnd]H carbene insertion – Cyclization sequence

Research output: Contribution to journal › Article › peer-review

MK.3010.2018 Chemistry

DOI

https://doi.org/10.1016/j.tetlet.2021.153269
Final published version

A short and practically convenient, modular approach to hitherto unknown dehydromorpholine sulfones and sulfonamides from α-acyl-α-diazomethyl sulfones and sulfonamides, respectively, has been developed. It involves Rh(II) carbene insertion into the O–H bond of 2-bromoethanol followed by thermally promoted tandem S_N2 displacement of the bromine atom by a primary amine and cyclodehydration.

Original language	English
Article number	153269
Number of pages	3
Journal	Tetrahedron Letters
Volume	78
Issue number	August
DOIs	https://doi.org/10.1016/j.tetlet.2021.153269
State	Published - 17 Aug 2021

Research areas

Alpha-Acyl-alpha-diazomethane sufones and solfamides, Dehydromorpholines, Privileged structures, Rh(II) carbene O-H insertion, Tandem SN2 – enamine formation, Tandem SN2-enamine formation

Scopus subject areas

Drug Discovery
Biochemistry
Organic Chemistry

ID: 84591832