Synthesis and chemistry of new benzoporphyrins

Add time:08/23/2019    Source:sciencedirect.com

Benzoporphyrins 5 and 6 are the major products obtained from the cycloaddition reactions of β-fused metallo-pyrroloporphyrins 1 and 2 with dimethyl acetylenedicarboxylate. In the presence of excess dienophile a bis-adduct is also obtained which undergoes retro-Diels-Alder reaction to produce 5. Benzoporphyrin 5 was converted into the first reported β-fused benzochlorins 9–11, and the free-base benzoporphyrin 12 was regioselectively brominated to afford 13. Exhaustive bromination also yields hexabromobenzoporphyrin 14.

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