Intramolecular [4 + 2] cycloadditions of hetarenynes and alkynes: An efficient strategy for the synthesis of polycyclic heteroaromatic compounds

ORGN 20

Javier E. Horta, jhorta@mit.edu and Rick L. Danheiser. Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Room 18-263, Cambridge, MA 02139
Terminally-substituted alkynes tethered to conjugated hetarenynes engage in intramolecular [4 + 2] cycloadditions resulting in polycyclic heteroaromatic compounds. The substrates that undergo these transformations are readily prepared by simple routes using easily accessible building blocks. The scope and limitations of this chemistry will be discussed, as well as the effects of structure and substitution on the rate and efficiency of the cycloaddition.

 

Heterocycles and Aromatics
8:00 AM-12:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- C301, Oral

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006