ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Regio- and Stereoselectivity of Aromatic and Heteroaromatic Nitrilimines in 1,3-Dipolar Cycloadditions

E. Jedlovská, Ľ. Fišera, and T. Liptaj

Department of Organic Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, SK-812 37 Bratislava

E-mail: eva.jedlovska@stuba.sk

Received: 3 December 2004

Abstract: The preparation of aromatic and heteroaromatic nitrilimines and the regio- and stereoselectivity of their subsequent 1,3-dipolar cycloadditions to various dipolarophiles (electron-rich or electron-poor mono- or disubstituted alkenes) are discussed. The cycloadditions to monosubstituted alkenes were highly regioselective and afforded only 5-substituted pyrazoles/pyrazolines, or mixtures of both, depending upon the nature of the dipolarophile, the type of substitution on nitrogen in nitrilimines, and the reaction conditions in each case.

Full paper in Portable Document Format: 595a354.pdf

Chemical Papers 59 (5) 354–361 (2005)