Fused polycyclic compounds via cycloaddition of 4-(1'-cyclohexenyl)-5-iodo-1,2,3-triazoles with 4-phenyl-1,2,4-triazoline-3,5-dione: the importance of a sacrificial iodide leaving group

Heather A Michaels; J Tyler Simmons; Ronald J Clark; Lei Zhu

doi:10.1021/jo400271j

Fused polycyclic compounds via cycloaddition of 4-(1'-cyclohexenyl)-5-iodo-1,2,3-triazoles with 4-phenyl-1,2,4-triazoline-3,5-dione: the importance of a sacrificial iodide leaving group

J Org Chem. 2013 May 17;78(10):5038-44. doi: 10.1021/jo400271j. Epub 2013 Apr 26.

Authors

Heather A Michaels¹, J Tyler Simmons, Ronald J Clark, Lei Zhu

Affiliation

¹ Department of Chemistry and Biochemistry, Florida State University, 95 Chieftan Way, Tallahassee, Florida 32306-4390, USA.

PMID: 23621085
DOI: 10.1021/jo400271j

Abstract

4-(1'-Cyclohexenyl)-5-iodo-1,2,3-triazole and 4-phenyl-1,2,4-triazoline-3,5-dione undergo a formal Diels-Alder reaction, which following an S(N)2' solvolysis process to displace the iodo group affords a fused polycyclic compound.

Publication types

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

MeSH terms

Cyclization
Iodides / chemistry*
Models, Molecular
Molecular Structure
Polycyclic Compounds / chemical synthesis*
Polycyclic Compounds / chemistry
Triazoles / chemistry*

Substances

Iodides
Polycyclic Compounds
Triazoles