Synthesis of meso,β-Fused Thiazinamine-Porphyrins via Oxidative C–N Fusion of Pyrimidinyl-Substituted Porphyrins
Résumé
5,15-Bis(pyrimidin-2-ylthio)porphyrins have been synthesized. Their electrochemical oxidation leads to the formation of the mono-and bis-C-N-fused thiopyrimidinium intermediates depending on the applied charge and potential. These latter undergo a nucleophilic attack with water during work-up that drives the ring opening of the pyrimidinium moiety. When piperidine is added before or after work-up, the neutral fused porphyrinthiazin-2-amines are generated and they exhibit a significant bathochromic shift of their Soret and Q bands.
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