A 1,3-Diaza-Claisen rearrangement that affords guanidines

Amy M Bowser; José S Madalengoitia

doi:10.1021/ol048575e

A 1,3-Diaza-Claisen rearrangement that affords guanidines

Org Lett. 2004 Sep 16;6(19):3409-12. doi: 10.1021/ol048575e.

Authors

Amy M Bowser¹, José S Madalengoitia

Affiliation

¹ Department of Chemistry, University of Vermont, Burlington, Vermont 05405, USA.

PMID: 15355064
DOI: 10.1021/ol048575e

Abstract

[reaction: see text] N-Alkyl-N'-tosylthioureas activated by EDCI react with azanorbonenes at room temperature through a 1,3-diaza-Claisen rearrangement, affording highly substituted, bicyclic guanidines in moderate to good yields.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Aza Compounds / chemistry*
Catalysis
Guanidines / analysis
Guanidines / chemical synthesis*
Indicators and Reagents
Molecular Structure
Norbornanes / chemistry

Substances

Aza Compounds
Guanidines
Indicators and Reagents
Norbornanes