Synthesis of 1-substituted benzo[c]isoxazol-3(1H)-imines via tandem nitroso-ene/intramolecular cyclizations of 2-nitrosobenzonitrile

ORGN 371

Jenna L Jeffrey, jjeffre1@uoregon.edu, Sean P. McClintock, smcclint@uoregon.edu, and Michael M. Haley, haley@uoregon.edu. Department of Chemistry and Materials Science Institute, University of Oregon, 1253 University of Oregon, Eugene, OR 97403
A new route to 1-substituted benzo[c]isoxazol-3(1H)-imines through the cyclization of 2-nitrosobenzonitrile is presented. Instead of reacting via the expected coarctate cyclization pathway, 2-nitrosobenzonitrile undergoes a tandem Nitroso-Ene/intramolecular cyclization to form benzo[c]isoxazol-3(1H)-imines under neutral conditions and at moderate temperatures. A variety of previously unknown cyclization products was synthesized in good yields, two of which were subsequently subjected to acid-catalyzed dimerization to form unusual, delocalized cationic systems. X-ray crystallographic data of one of the dibenzo[c]isoxazolium salts indicates a cationic pocket with a unique, U-shaped geometry ideal for chelating anions or metals.

 

Heterocycles and Aromatics, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, April 8, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008