Mechanism of the inverse electron demand Diels-Alder reaction of 2-aminopyrroles with 1,3,5-triazines: Identification of five intermediates by 1H, 13C, 15N and 19F NMR spectroscopy

ORGN 423

Michael De Rosa, mxd19@psu.edu and David Arnold. Department of Chemistry, The Pennsylvania State University Delaware County Campus, 25 Yearsley Mill Road, Media, PA 19063
A cascade mechanism has been proposed for the inverse electron demand Diels-Alder (IEDDA) reaction. However in only a few examples has an intermediate been observed or isolated. When the IEDDA reaction of 1-t-butyl-2-aminopyrrole (1) with 2,4,6-tris(trifluoromethyl)-1,3,5-triazine (2) in THF-d8 to give pyrrolo[2,3-d]pyrimidine (8) was studied by 1H, 13 C, 15N and 19F NMR spectroscopy, five intermediates (4-7) were identified. Intermediate 5 is a cul-de-sac as there is not an obvious mechanism from it to the final product. The following mechanism summarizes the results of our spectral studies. This work was supported by a grant (CHE-0110801) from the National Science Foundation.

 

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