HETEROCYCLES

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■ Novel Photocleavable Structures I: Synthesis of Hydroxyalkylphenone Analogues Electron-rich Heterocycles

Robert Liska

*Institute of Chemical Technology of Organic Materials, University of Technology Vienna, Getreidemarkt 9/162, 1060 Vienna, Austria

Abstract

A series of photoinitiating compounds with the general structure ArCOCMe₂OH, where Ar is 2-furyl (1a), 3-furyl (1b), 2-thienyl (2a), 3-thienyl (2b), 2-pyrrolyl (3a) and 3-pyrrolyl (3b), were prepared. The heterocyclic precursors were substituted by Friedel-Crafts type reaction with isobutyric acid derivatives. Subsequent bromination and hydrolysis gave 1a, 2a and 3b. Derivatives 1b, 2b and 3a were obtained by reaction of organometallic intermediates of heterocyclic precursors with suitable nitriles or esters.