Diels-Alder Reactions of Nitrobenzofurans: A Simple Dibenzofuran Synthesis. Theoretical studies using DFT Methods

CLAUDIA D. DELLA ROSA; JUAN P. SANCHEZ; MARÍA N. KNEETEMAN; PEDRO M.E. MANCINI

TETRAHEDRON LETTERS

PERGAMON-ELSEVIER SCIENCE LTD

Lugar: Amsterdam; Año: 2011 vol. 52 p. 2316 - 2319

0040-4039

2- and 3-nitrobenzofurans are studied in polar thermal Diels?Alder reactions with normal electron demand using several structurally different dienes. A very strong electron-acceptor group, such as the nitro group, pushes the dienophilic character of these heterocyclic compounds. Since this substituent is easily extruded under thermal conditions, this reaction sequence becomes a simple method for the preparation of families of organic compounds with heteroatom rings. Part of this work is specifically concerned with theoretical studies using DFT methods. The global and local electrophilicity and nucleophilicity indices were calculated for the dienophiles and dienes used in this study. When 2-nitrobenzofuran and 3-nitrobenzofuran were reacted with isoprene, 1-trimethylsilyloxy-1,3-butadiene and Danishesfky?s diene, under different thermal reaction conditions they showed their dienophilic character taking part in normal-demand polar DA cycloaddition reactions.