Synthesis of highly substituted aniline and o-phenylenediamine derivatives containing various substitution patterns

Kristof Kranjc; Bogdan Stefane; Slovenko Polanc; Marijan Kocevar

doi:10.1021/jo035473d

Synthesis of highly substituted aniline and o-phenylenediamine derivatives containing various substitution patterns

J Org Chem. 2004 Apr 30;69(9):3190-3. doi: 10.1021/jo035473d.

Authors

Kristof Kranjc¹, Bogdan Stefane, Slovenko Polanc, Marijan Kocevar

Affiliation

¹ Faculty of Chemistry and Chemical Technology, University of Ljubljana, Slovenia.

PMID: 15104462
DOI: 10.1021/jo035473d

Abstract

The Diels-Alder reactions of a variety of 2H-pyran-2-ones 1 with alkynes 2 yielding highly substituted aniline and o-phenylenediamine derivatives 4 with novel (and in some cases known but very rare and useful) structural patterns are presented. The effect of substituents of both reactants on the reaction rates was investigated. The reactions were carried out under thermal conditions, as well as at high pressures.